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  • 51.
    Cheruku, Pradeep
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Ali, Muhammad
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Neudoerfl, Joerg-M
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Development of new thiazole-based iridium catalysts and their applications in the asymmetric hydrogenation of trisubstituted olefins2008In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 6, no 2, p. 366-373Article in journal (Refereed)
    Abstract [en]

    New thiazole-based chiral N,P-ligands that are open-chain analogues of known cyclic thiazole ligands have been synthesized and evaluated in the iridium-catalyzed asymmetric hydrogenation of trisubstituted olefins. Chirality was introduced into the ligands through a highly diastereoselective alkylation using Oppolzer's camphorsultam as chiral auxiliary. In general, the new catalysts are as reactive and selective as their cyclic counterparts for the asymmetric hydrogenation of various trisubstituted olefins.

  • 52.
    Cheruku, Pradeep
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Church, Tamara
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Phosphine-Free Cp*Ru(Diamine) Catalysts in the Hydrogenation of Imines2008In: Chemistry - An Asian Journal, ISSN (Print)1861-4728.(Online)1861-471X, Vol. 3, no 8-9, p. 1390-1394Article in journal (Refereed)
    Abstract [en]

    We previously reported the phosphine-free Cp*Ru(diamine)-catalyzed hydrogenation of aryl methyl ketones. Herein we present the first report of ruthenium-diamine-catalyzed imine hydrogenation to form amines. The most effective catalyst, I/KOtBu, completely converted several imines to amines at room temperature. The effect of electron-donating and -with- drawing groups on the reaction was investigated using a suitable series of substrates. The asymmetric version of the reaction was studied for two substrates, and the chiral amine products could be obtained in moderate enantiomeric excess.

  • 53.
    Cheruku, Pradeep
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Diesen, Jarle
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Asymmetric Hydrogenation of Di and Trisubstituted Enol Phosphinates with N,P-Ligated Iridium Complexes2008In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, no 16, p. 5595-5599Article in journal (Refereed)
    Abstract [en]

    The iridium-catalyzed asymmetric hydrogenation of various di- and trisubstituted enol phosphinates has been studied. Excellent enantioselectivities (up to >99% ee) and full conversion were observed for a range of substrates with both aromatic and aliphatic side chains. Enol phosphinates are structural analogues of enol acetates, and the hydrogenated alkyl phosphinate products can easily be transformed into the corresponding alcohols with conservation of stereochemistry. We have also hydrogenated, in excellent ee, several purely alkyl-substituted enol phosphinates, producing chiral alcohols that are difficult to obtain highly enantioselectively from ketone hydrogenations.

  • 54. Diéguez, Montserrat
    et al.
    Mazuela, Javier
    Pàmies, Oscar
    Verendel, J Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Andersson, Pher G
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Chiral pyranoside phosphite-oxazolines: a new class of ligand for asymmetric catalytic hydrogenation of alkenes2008In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, no 23, p. 7208-7209Article in journal (Refereed)
    Abstract [en]

    We have described the first successful application of a phosphite-oxazoline ligand library in the asymmetric Ir-catalyzed hydrogenation of several unfunctionalized olefins. The introduction of a bulky biaryl phosphite moiety in the ligand design is highly adventitious in the product outcome. By carefully selecting the ligand components, we obtained high activities (TOFs up to >1500 mol x (mol x h)(-1) at 1 bar of H2) and enantioselectivities (ee values up to >99%) and, at the same time, show a broad scope for different substrate types. So, this is an exceptional ligand class that competes favorably with a few other ligand series that also provide high ee values for tri- and disubstituted substrate types.

  • 55. Diéguez, Montserrat
    et al.
    Mazuela, Javier
    Pàmies, Oscar
    Verendel, Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Biaryl phosphite-oxazolines from hydroxyl aminoacid derivatives: highly efficient modular ligands for Ir-catalyzed hydrogenation of alkenes2008In: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, no 33, p. 3888-3890Article in journal (Refereed)
    Abstract [en]

    High enantioselectivities and activities are achieved in the Ir-catalyzed hydrogenation of several unfunctionalized olefins using modular biaryl phosphite-oxazoline ligands from hydroxyl aminoacid derivatives, the presence of a biaryl phosphite group is crucial to this success.

  • 56.
    Diéguez, Montserrat
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Mazuela, Javier
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Pàmies, Oscar
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Verendel, Johan
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Chiral Pyranoside Phosphite - Oxazolines: A New Class of Ligand for Asymmetric Catalytic Hydrogenation of Alkenes2008In: J. Am. Chem. Soc., no 130, p. 7208-7209Article in journal (Refereed)
  • 57.
    Ekegren, Jenny
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Modin, Stefan
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Alonso, Diego
    Andersson, Pher
    Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Multigram scale synthesis of a useful aza-Diels-Alder adduct in a one-step procedure2002In: Tetrahedron Asymmetry, no 13, p. 447-449Article in journal (Refereed)
  • 58.
    Ekegren, Jenny
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Roth, Peter
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Källström, Klas
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tarnai, Tibor
    Andersson, Pher
    Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Synthesis and evaluation of N,S-compounds as chiral ligands for transfer hydrogenation of acetophenone2003In: Org. Biomol. Chem, no 1, p. 358-366Article in journal (Refereed)
  • 59.
    Engdahl, Carin
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Eklund, Ulf
    UMEA UNIV, DEPT ORGAN CHEM, NMR RES GRP, S-90187 UMEA, SWEDEN .
    Long‑Range Deuterium Isotope Effects on 13C NMR Shifts of Intramolecularly Hydrogen‑Bonded 9‑Hydroxyphenalen‑1‑ones1991In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 29, no 1, p. 54-62Article in journal (Refereed)
    Abstract [en]

    The 1H and 13C NMR spectra of 9-hydroxyphenalenone (1) and 9-hydroxy-2-methylphenalenone (2) have been completely assigned. Primary and secondary deuterium isotope effects were determined in three solvents (chloroform, acetone and dimethyl sulphoxide), including the effect of temperature on the secondary isotope effects. Both negative and large long-range secondary isotope effects were found for both 1 and 2. The average secondary isotope effects for corresponding carbons follow the same sign and magnitude pattern in both compounds.

  • 60.
    Engman, Lars
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Compositions and Methods.2009Patent (Other (popular science, discussion, etc.))
  • 61.
    Engman, Lars
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Holmgren, Arne
    Vlamis-Gardikas, A.
    Zhao, R.
    Kandasamy, K.
    Hoffner, S.
    Bacterial Thioredoxin Reductase Inhibitors and Methods for Use Thereof2009Patent (Other (popular science, discussion, etc.))
    Abstract [en]

    The mechanism of action of Ebselen differentiates between bacterial and mammalian thioredoxin reductase (TrxR). It displays fast oxidation of mammalian Trx and via the NADPH-TrxR catalyzed turnover of ebselen selenol with hydrogen peroxide, and therefore are mammalian antioxidants. Ebselen, and its diselenide, are strong competitive inhibitors of E. coli TrxR with K.sub.i of 0.14 .mu.M and 0.46 .mu.M, respectively. E. coli mutants lacking glutathione reductase or glutathione were much more sensitive to inhibition by ebselen. Since either glutaredoxin or thioredoxin systems are electron donors to ribonucleotide reductase, ebselen targets primarily glutathione and glutaredoxin-negative bacteria, a class which includes major pathogens. Ebselen, and similar compounds are therefore useful as antibacterial agents, even for multiresistant strains. Two major pathogenic bacteria, which previously had not been known to be sensitive to ebselen, Mycobacterium tuberculosis (tuberculosis) and Helicobacter pylori (stomach ulcer and cancer), were shown to be excellent targets. Helicobacter pylori was also sensitive to ebsulfur.

  • 62.
    Engman, Lars
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Johansson, Henrik
    Antioxidants for use in therapy. 2009Patent (Other (popular science, discussion, etc.))
  • 63.
    Engman, Lars
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Wojtón, A
    Oleksyn, B. J
    Sliwinski, J
    The crystal structure of 2-[N,N-dimethylamino)methyl] benzenetellurenyl chloride2004In: Phosphorus, Sulfur, and Silicon, ISSN 1042-6507, Vol. 179, p. 285-292Article in journal (Refereed)
    Abstract [en]

    The crystal structure of 2-[(N,N-dimethylamino)methyl]benzenetellurenyl chloride (2), a compound previously formulated as bis [[2-(N,N-dimethylamino)methyl]phenyl] ditelluride bis hydrochloride (1a), was determinded. In the molecule 2, tellurium is bonded to the carbon of the phenyl group [2.120(3)Å], the nitrogen o fthe ortho dimethylamino substituent [2.362(3)Å], and the chlorine atom [2.536[1]Å]. There also is an intermolecular interaction of the tellurium atom with the phenyl ring of a neighbouring molecule [3.655(1)Å], resulting in the formation of zigzag chains along the b axis. The noncentorsymmetric space group of the crystal can be explained by the chiral surrounding of tellurium.

  • 64.
    Erdélyi, Máté
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Organic Pharmaceutical Chemistry.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Rapid homogeneous-phase Sonogashira coupling reactions using controlled microwave heating2001In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 66, no 12, p. 4165-4169Article in journal (Refereed)
    Abstract [en]

    A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with trimethylsilylacetylene. Excellent yields (80−95%) for substrates containing a large variety of substituents in different positions are obtained in 5−25 min.

  • 65.
    Ericsson, Cecilia
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Engman, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Microwave-Assisted Group-Transfer Cyclization of Organotellurium Compounds2004In: The Journal of Organic Chemistry, Vol. 69, no 15, p. 5143-5146Article in journal (Refereed)
    Abstract [en]

    Primary- and secondary-alkyl aryl tellurides, prepared by arenetellurolate ring-opening of epoxides/O-allylation, were, found to undergo rapid (3-10 min) group-transfer cyclization to afford tetrahydrofuran derivatives in 60-74% yield when heated in a microwave cavity at 250C in ethylene glycol or at 180C in water. To go to completion, similar transformations had previously required extended photolysis in refluxing benzene containing a substantial amount of hexabutylditin. The only drawback of the microwave-assisted process was the loss in diastereoselectivity wich is a consequence of the higher reaction temperature. Substitution in the Te-aryl moiety of the secondary-alkyl aryl tellurides (4-OMe, 4-H, 4-CF3) did not affect the outcome of the group-transfer reaction in ethylene glycol. However, at lower temperature, using water as a solvent, the CF3 derivative failed to react. The microwave-assisted grouptransfer cyclization was extended to benzylic but not to primary- and secondary-alkyl phenyl selenides.

  • 66. Eriksson, Per
    et al.
    Engman, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Lind, Johan
    Merényi, Gabor
    Aqueous Phase One-Electron Reduction of Sulfonium, Selenonium and Telluronium Salts2005In: Eur. J. Org. Chem., p. 701-705Article in journal (Refereed)
    Abstract [en]

    Triorganylsulfonium, -selenonium and -telluronium salts were reduced by carbon dioxide radical anions/solvated electrons produced in aqueous solution by radiolysis. The radical expulsion accompanying reduction occurred with the expected leaving group propensities (benzyl > secondary alkyl> primary alkyl> methy> phenyl), although greater than expected loss of the phenyl group was often observed. Diorganyl chalcogenides formed in the reductions were conveniently isolated by extraction with an organic solvent. Product yields based on the amount of reducing radicals obtained from the y-source were often higher than stoichiometric (up to 1800%) in the reduction of selenonium an dtelluronium compounds; it is likely that this result can be accounted for in terms of a chain reaction with carbon-centred radicals/formate serving as the chain transfer agent. The product distribution was essentially independent of the reducing species for diphenyl alkyl telluronium salts, whereas significant variations were seen for some of the corresponding selenonium salts. This would suggest the intermediacy of telluranyl radicals in the one-electron reduction of telluronium salts. However, pulse radiolysis experiments indicated that the lifetimes of such a species (the triphenyltelluranyl radical) would have to be less than 1 us.

  • 67.
    Ersmark, Karolina
    et al.
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Nervall, Martin
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Gutiérrez-de-Terán, Hugo
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Hamelink, Elizabeth
    Janka, Linda K.
    Clemente, Jose C.
    Dunn, Ben M.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Samuelsson, Bertil
    Åqvist, Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Hallberg, Anders
    Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Cell and Molecular Biology, Structural Molecular Biology.
    Macrocyclic inhibitors of the malarial aspartic proteases plasmepsin I, II, and IV2006In: Biorganic & Medicinal Chemistry, no 14, p. 2197-2208Article in journal (Refereed)
  • 68.
    Gayet, Arnaud
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Kinetic resolution of racemic epoxides using a chiral diamine catalyst2005In: Tetrahedron Letters, no 46, p. 4805-4807Article in journal (Refereed)
  • 69.
    Gayet, Arnaud
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bertilsson, Sophie
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Novel Catalytic Kinetic Resolution of Racemic Epoxides to Allylic Alcohols2002In: Organic Letters, Vol. 4, no 22, p. 3777-3779Article in journal (Refereed)
  • 70.
    Gayet, Arnaud
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Bolea, Christine
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Development of new camphor based N,S chiral ligands and their application in transfer hydrogenation2004In: Organic & Biomolecular Chemistry, no 2, p. 1887-1893Article in journal (Refereed)
  • 71.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Gomes, João
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bergkvist, Magnus
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Grennberg, Helena
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Configurational Assignment of Acyclic (π-Allyl)Palladium Complexes: Analytical Application of Chelating Nitrogen Ligands1995In: Organometallics, ISSN 0276-7333, E-ISSN 1520-6041, Vol. 14, no 3, p. 1354-1364p. 1354-1364Article in journal (Refereed)
    Abstract [en]

    A method for assignment of the relative stereochemistry in acyclic pi-allyl)palladium complexes by H-1 NMR H-H coupling constants has been developed. It is based on the introduction of nitrogen chelating ligands of the bipyridyl type into the complexes. The analytical suitability of several other types of nitrogen chelating ligands has also been investigated. A model for rationalization of the observed relation between stereochemistry and spectral parameters is proposed. Introduction of the chelating ligand also affects the syn,anti equilibrium of the complexes. Isomer ratios depend upon the relative stereochemistry of the side chain as well as on the chelating ligand.

  • 72.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Oscarsson, Sven
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Biochemistry.
    Reaction of pyridine derivatives with butyl glycidyl ether as a model system for glycidyl ether modified agarose: structural assignment by selective inept spectra1990In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 46, no 7, p. 2539-2548Article in journal (Refereed)
    Abstract [en]

    The reaction of 2-thio-pyridine N-oxide, 2-amino-, 2-hydroxy, 2-thio-, and 4-thiopyridine with butyl glycidyl ether was investigated as a model system for the functionalization of 2,3-epoxypropyl activated agarose. Unambiguous structural assignment of the products was provided by selective INEPT and nuclear Overhauser difference spectra. All reactions were shown to give only one of the possible regioisomers. Further conclusions regarding the structure of the agarose derivatives were drawn from IR spectra.

  • 73.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Plobeck, Niklas A.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Comparison of one- and two-dimensional techniques in the unambiguous 13C NMR spectral assignment of ellipticine and related indole derivatives1990In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 28, p. 635-641Article in journal (Refereed)
    Abstract [en]

    The 13C NMR spectra of several indole derivatives have been completely assigned by reverse detected one-bond and long-range CH correlation spectra (HMQC) and by selective INEPT experiments. The resolution and sensitivity of the two techniques are discussed. As a result, the literature assignments for the previously known compounds have been revised.

  • 74.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tanner, David
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Complete 1H and 13C NMR spectral assignment of venturicidin A by 2D NMR spectroscopy1989In: Magnetic Resonance in Chemistry, ISSN 0749-1581, E-ISSN 1097-458X, Vol. 27, no 9, p. 863-871Article in journal (Refereed)
    Abstract [en]

    After correlation of the majority of signals by COSY and one-bond heteronuclear correlation, the complete assignment of the 1H and 13C NMR spectra of the macrolide antibiotic venturicidin A required the application of long-range CH coupling information. This was accessible by the COLOC-S and selective INEPT experiments, and the sensitivity of these experiments is discussed. Steric information was obtained from a NOESY spectrum, and the solution structure compared with that in the crystal.

  • 75.
    Gogoll, Adolf
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Tegenfeldt, Jörgen
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Materials Chemistry, Inorganic Chemistry.
    Oscarsson, Sven
    UNIV UPPSALA, CTR BIOMED, INST BIOCHEM, S-75123 UPPSALA, SWEDEN .
    CP/MAS carbon-13 NMR spectroscopy of epoxypropyl-activated agarose functionalized with pyridine derivatives1991In: Macromolecules, ISSN 0024-9297, E-ISSN 1520-5835, Vol. 24, no 16, p. 4727-4728Article in journal (Refereed)
  • 76.
    Gogoll, Adolf
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Toom, Lauri
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Grennberg, Helena
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Ligand-Induced Formation of an Adamantanoid Hexanuclear (π-Allyl) PdII(μ3-Hydroxo) Cluster Stacked as Hydrogen-Bonded Double Strands2005In: Angew. Chem. Int. Ed., no 44, p. 2295-2300Article in journal (Refereed)
  • 77.
    Govender, Thavendran
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Hojabri, Leila
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Matloubi Moghaddam, Firouz
    Arvidsson, Per I.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Organocatalytic synthesis of chiral benzopyrans2006In: Tetrahedron: Asymmetry, no 17, p. 1763-1767Article in journal (Refereed)
    Abstract [en]

    Benzopyrans, or chromenes, are widespread in nature and are considered to be a privileged scaffold in medicinal chemistry. Herein, we report the first organocatalyzed asymmetric synthesis of chiral benzopyrans. The benzopyran unit is constructed through a domino reaction involving an oxa-Michael attack of salicylic aldehyde derivatives onto a,B-unsaturated aldehydes, activated through iminium-ion formation with the organocatalyst, followed by an intramolecular aldol reaction and subsequent elimination of water. This overall reaction sequence provides benzopyrans with aromatic C-2 substituents in up to 60% enantioselectivity, while C-2 aliphatic analogues can be obtained in 90% enantiomeric excess, but with only 20% yield. The role of additives, as well as the possible racemization of the benzopyran, was also investigated.

  • 78. Guijarro, David
    et al.
    Pinho, Pedro
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Enantioselective Addition of Dialkylzinc Reagents to N-(Diphenylphosphinoyl) Imines Promoted by 2-Azanorbornylmethanols1998In: J. Org. Chem., no 63, p. 2530-2535Article in journal (Refereed)
  • 79.
    Hedberg, Christian
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Catalytic Asymmetric Total Synthesis of Muscarinic Receptor Antagonist (R)-Tolterodine2005In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 347, no 5, p. 662-666Article in journal (Refereed)
    Abstract [en]

    A convenient and high yielding method for the preparation of (R)-tolterodine, utilizing a catalytic asymmetric Me-CBS reduction was developed. Highly enantioenriched (R)-6-methyl-4-phenyl-3,4-dihydrochromen-2-one (94% ee) was recrystallized to yield practically enantiopure material (ee >99%) and converted to (R)-tolterodine in a four-step procedure. The configuration of the crucial stereocenter was preserved during the synthesis and the obtained product was identified by chiral HPLC to be the (R)-tolterodine enantiomer.

  • 80.
    Hedberg, Christian
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Källström, Klas
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Arvidsson, Per
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Brandt, Peter
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Mechanistic Insights into the Phosphine-Free RuCp*-Diamine-Catalyzed Hydrogenation of Aryl Ketones: Experimental and Theoretical Evidence for an Alcohol-Mediated Dihydrogen Activation2005In: J. Am. Chem. Soc., no 127, p. 15083-15090Article in journal (Refereed)
    Abstract
  • 81. Henriksen, Signe
    et al.
    Norrby, Per-Ola
    Kaukoranta, Päivi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Combined Experimental and Theoretical Study of the Mechanism and Enantioselectivity of Palladium-Catalyzed Intermolecular Heck Coupling2008In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 130, no 31, p. 10414-10421Article in journal (Refereed)
    Abstract [en]

    The asymmetric Heck reaction using P,N-ligands has been studied by a combination of theoretical and experimental methods. The reaction follows Halpern-style selectivity, that is, the major isomer is produced from the least favored form of the pre-insertion intermediate. The initially formed Ph-Pd(P,N) species prefers a geometry with the phenyl trans to N. However, the alternative form, with Ph trans to P, is much less stable but much more reactive. In the preferred transition state, the phenyl moiety is trans to P, but significant electron density has been transferred to the alkene carbon trans to N. The steric interactions in this transition state fully account for the enantioselectivity observed with the ligands studied. The calculations also predict relative reactivity and nonlinear mixing effects for the investigated ligands, these predictions are fully validated by experimental testing. Finally, the low conversion observed with some catalysts was found to be caused by inactivation due to weak binding of the ligand to Pd(0). Adding monodentate PPh3 alleviated the precipitation problem without deteriorating the enantioselectivity and led to one of the most effective catalytic systems to date.

  • 82. Holmgren, Arne
    et al.
    Lu, Jun
    Vlamis-Gardikas, Alexios
    Zhao, Rong
    Kandasamy, Karuppasamy
    Engman, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Hoffner, Sven
    Bacterial Thioredoxin Reductase Inhibitors and Methods for Use Thereof2007Patent (Other (popular scientific, debate etc.))
  • 83.
    Huang, Hao
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Karlsson, Christoffer
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Strømme, Maria
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Sjödin, Martin
    Uppsala University, Disciplinary Domain of Science and Technology, Technology, Department of Engineering Sciences, Nanotechnology and Functional Materials.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Hydroquinone–pyrrole dyads with varied linkers2016In: Beilstein Journal of Organic Chemistry, ISSN 2195-951X, E-ISSN 1860-5397, Vol. 12, p. 89-96Article in journal (Refereed)
    Abstract [en]

    A series of pyrroles functionalized in the 3-position with p-dimethoxybenzene via various linkers (CH2, CH2CH2, CH=CH, C≡C) has been synthesized. Their electronic properties have been deduced from 1H NMR, 13C NMR, and UV–vis spectra to detect possible interactions between the two aromatic subunits. The extent of conjugation between the subunits is largely controlled by the nature of the linker, with the largest conjugation found with the trans-ethene linker and the weakest with the aliphatic linkers. DFT calculations revealed substantial changes in the HOMO–LUMO gap that correlated with the extent of conjugation found experimentally. The results of this work are expected to open up for use of the investigated compounds as components of redox-active materials in sustainable, organic electrical energy storage devices.

  • 84.
    Kocovsky, Pavel
    et al.
    UNIV UPPSALA, DEPT ORGAN CHEM, BOX 531, S-75121 UPPSALA, SWEDEN .
    Langer, Vratislaw
    CHALMERS UNIV TECHNOL, DEPT INORGAN CHEM, S-41296 GOTHENBURG, SWEDEN .
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Structural Requirements for the Thallium(III)‑mediated Cyclisation of Unsaturated Alcohols: A Novel Fragmentation Reaction Producing 19‑Norsteroids1990In: Journal of the Chemical Society. Chemical communications, ISSN 0022-4936, Vol. 15, p. 1028-1028Article in journal (Refereed)
    Abstract [en]

    The unsaturated alcohol (1) is readily cyclised to the hydroxytetrahydrofuran (3) by means of thallium(III), whereas its congener (4) has been found to give (7) as the product of a novel, stereoelectronically controlled, fragmentation; the scope of the tandem electrophilic cyclisation/solvolysis is discussed; the structure of (7) has been determined by X-ray crystallography.

  • 85. Kolb, Hartmuth
    et al.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bennani, Youssef
    Crispino, Gerard
    Jeong, Kyu-Sung
    Kwong, Hoi-Lun
    Sharpless, K. Barry
    On1993In: J. Am. Chem. Soc., no 115, p. 12226-12227Article in journal (Refereed)
  • 86. Kolb, Hartmuth
    et al.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Sharpless, K. Barry
    Toward an Understanding of the High Enantioselectivity in the Osmium-Catalyzed Asymmetric Dihydroxylation (AD). 1. Kinetics1994In: J. Am. Chem. Soc., no 116, p. 1278-1291Article in journal (Refereed)
  • 87. Koroleva, Elise B.
    et al.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Development of an Asymmetric Palladium-Catalysed Elimination1996In: Tetrahedron Asymmetry, Vol. 7, no 9, p. 2467-2470Article in journal (Refereed)
  • 88. Koroleva, Elise B.
    et al.
    Bäckvall, Jan-E.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Palladium-Catalyzed Stereocontrolled endo Cyclization of 3-hydroxypropyl-1,3-cyclohexadiene Leading to Versatile Fused Tetrahydropyrans1995In: Tetrahedron Letters, Vol. 36, no 30, p. 5397-5400Article in journal (Refereed)
  • 89.
    Kočovský, Pavel
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry.
    Pour, Milan
    CZECHOSLOVAK ACAD SCI, INST ORGAN CHEM & BIOCHEM, CS-16610 PRAGUE 6, CZECH REPUBLIC.
    Gogoll, Adolf
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Hanuš, Vladimir
    CZECHOSLOVAK ACAD SCI, J HEYROVSKY INST PHYS CHEM & ELECTROCHEM, CS-18223 PRAGUE 8, CZECH REPUBLIC .
    Smrcina, M.
    CZECHOSLOVAK ACAD SCI, J HEYROVSKY INST PHYS CHEM & ELECTROCHEM, CS-18223 PRAGUE 8, CZECH REPUBLIC .
    Corner Attack on Cyclopropane by Thallium(III) Ions: A Highly Stereospecific Cleavage and Skeletal Rearrangement of 3a,5‑Cyclo‑5a‑cholestan‑6a‑ol1990In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 112, no 18, p. 6735-6737Article in journal (Refereed)
  • 90.
    Kumar, Sangit
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Engman, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Microwave-Assisted Copper-Catalyzed Preparation of Diaryl Chalcogenides2006In: J. Org. Chem., Vol. 71, p. 5400-5403Article in journal (Refereed)
  • 91.
    Källström, Klas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Asymmetric hydrogenation of tri-substituted alkenes with Ir-NHC-thiazole complexes2006In: Tetrahedron Letters, ISSN 0040-4039, E-ISSN 1359-8562, Vol. 47, no 42, p. 7477-7480Article in journal (Refereed)
    Abstract [en]

    An efficient chiral N-heterocyclic carbene ligand for the Ir-catalyzed asymmetric hydrogenation of largely unfunctionalized tri-substituted olefins has been developed. The Ir-NHC-thiazole catalyst is able to reduce a large variety of substrates with excellent conversions and good enantioselectivities with ee's ranging from 34% to 90%, depending on the geometry around the double bond of the substrates.

  • 92.
    Källström, Klas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Hedberg, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Brandt, Peter
    Bayer, Annette
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry. Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Rationally Designed LIgands for Asymmetric Iridium-Catalyzed Hydrogenation of Olefins2004In: J. Am. Chem. Soc., no 126, p. 14308-14309Article in journal (Refereed)
    Abstract
  • 93.
    Källström, Klas
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Munslow, Ian
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Ir-Catalysed Asymmetric Hydrogenation: Ligands, Substrates and Mechanism2006In: Chem. Eur. J., no 12, p. 3194-3200Article in journal (Refereed)
  • 94.
    Källström, Klas
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Munslow, Ian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Hedberg, Christian
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Andersson, Pher
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Iridium-Catalysed Asymmetric Hydrogenation of Vinylsilanes as a Route to Optically Active Silanes2006In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 348, no 18, p. 2575-2578Article in journal (Refereed)
    Abstract [en]

    The first use of vinylsilanes as substrates in the asymmetric iridium-catalysed hydrogenation is reported, providing products with enantioselectivities of up to 98%.

  • 95.
    Li, Junxin
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Grennberg, Helena
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry. Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Microwave-Assisted Covalent Sidewall Functionalization of Multiwalled Carbon Nanotubes2006In: Chem. Eur. J., no 12, p. 3869-3875Article in journal (Refereed)
  • 96.
    Magnus, Angelika
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Bertilsson, Sophie
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Andersson, Pher
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Asymmetric base-mediated epoxide isomerisation2002In: Chem. Soc. Rev, no 31, p. 223-229Article in journal (Refereed)
  • 97.
    Mazuela, Javier
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Paptchikhine, Alexander
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Pàmies, Oscar
    Andersson, Pher G
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Diéguez, Montserrat
    Adaptative Biaryl Phosphite-Oxazole and Phosphite-Thiazole Ligands for Asymmetric Ir-Catalyzed Hydrogenation of Alkenes2010In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 16, no 15, p. 4567-4576Article in journal (Refereed)
    Abstract [en]

    A library of readily available phosphite-oxazole/thiazole ligands (L1 a-g-L7 a-g) was applied in the Ir-catalyzed asymmetric hydrogenation of several largely unfunctionalized E- and Z-trisubstituted and 1,1-disubstituted terminal alkenes. The ability of the catalysts to transfer chiral information to the product could be tuned by choosing suitable ligand components (bridge length, the substituents in the heterocyclic ring and the alkyl backbone chain, the configuration of the ligand backbone, and the substituents/configurations in the biaryl phosphite moiety), so that enantioselectivities could be maximized for each substrate as required. Enantioselectivities were therefore excellent (enantiomeric excess (ee) values up to >99 %) for a wide range of E- and Z-trisubstituted and 1,1-disubstituted terminal alkenes. The biaryl phosphite moiety was a very advantageous ligand component in terms of substrate versatility.

  • 98.
    Mazuela, Javier
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Verendel, J Johan
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Coll, Mercedes
    Schäffner, Benjamín
    Börner, Armin
    Andersson, Pher G
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry, Organic Chemistry I.
    Pàmies, Oscar
    Diéguez, Montserrat
    Iridium phosphite-oxazoline catalysts for the highly enantioselective hydrogenation of terminal alkenes2009In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 131, no 34, p. 12344-12353Article in journal (Refereed)
    Abstract [en]

    A modular library of readily available phosphite-oxazoline ligands (L1-L16a-f) has been successfully applied for the first time in the Ir-catalyzed asymmetric hydrogenation of a broad range of highly unfunctionalized 1,1,-disubstituted terminal alkenes. Enantioselectivities up to >99% and full conversions were obtained in several 1,1-disubstituted alkenes, including substrate classes that have never been asymmetrically hydrogenated before (i.e., 1,1-heteoraryl-alkyl, 1,1-diaryl, trifluoromethyl, etc.). The results indicated that these catalytic systems have high tolerance to the steric and electronic requirements of the substrate and also to the presence of a neighboring polar group. The asymmetric hydrogenations were also performed using propylene carbonate as solvent, which allowed the Ir catalyst to be reused and maintained the excellent enantioselectivities.

  • 99. McNaughton, Michael
    et al.
    Engman, Lars
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Birmingham, A.
    Powis, G.
    Cotgreave, I.A.
    Cyclodextrin-Derived Diorganyl Tellurides as Glutathione Peroxidase Mimics and Inhibitors of Thioredoxin Reductase and Cancer Cell Growth2004In: J. Med. Chem., no 47, p. 233-239Article in journal (Refereed)
  • 100.
    Modin, Judit
    et al.
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Johansson, Henrik
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    Grennberg, Helena
    Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry I. Organisk kemi.
    New Pyrazolino- and Pyrrolidino[60]fullerenes with Transition-Metal Chelating Pyridine Substitutents: Synthesis and Complexation to Ru(II)2005In: Organic Letters, Vol. 7, no 18, p. 3977-3979Article in journal (Refereed)
    Abstract [en]

    Three pyridine-substituted fullerene adducts, bis(2,2'-bipyridine)(2'-phenyl-5'-(2-pyridinyl)-2'H-[5.6]fullereno(C60-Ih)[1,9]pyrazole)ruthenium-bis-(hexafluorphosphate) (1), bis(2,2'-bipyridine)(2'-phenyl-5'-(4-(4'-methyl-2,2'-bipyridinyl)-2'H[5,6]fulleroneo(C60-Ih)[1,9]pyrazole)ruthenium-bis(hexafluorophosphate)(2), and bis(2,2'-bipyridine)(1',5'-dihydro-3'-methyl-2'-(4(4'-methyl-2,2'-bipyridinyl))-2'H-[5,6]fullereno(C60-Ih)[1,9]pyrrole)ruthenium-bis(hexafluorophosphate) 83), have been prepared. The common features for these complexes are the short bridges between he fullerene and the pyridine moities.

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