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  • 1. Bremberg, U
    et al.
    Lutsenko, S
    Kaiser, N F
    Larhed, M
    Hallberg, A
    Mobert, C
    Rapid and stereoselective C-C, C-O, C-N and C-S couplings via microwave accelerated palladium-catalyzed allylic substitutions2000Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 7, s. 1004-1008Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Palladium-catalyzed substitution of cyclohex-2-en-1-yl ethyl carbonate with neutral C-, O-, and N-nucleophiles was achieved in 1-2 minutes using microwave flash hearing. Enantioselectivities up to 96% were observed. Ionic nucleophiles tended to result in lower ee. With S-nucleophiles problems with the stability of the nucleophile were encountered.

  • 2.
    Cadu, Alban
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Paptchikhine, Alexander
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Birch Reaction Followed by Asymmetric Iridium-Catalysed Hydrogenation2011Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 23, s. 3796-3800Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Birch reaction products are asymmetrically hydrogenated with high enantio- and diastereoselectivity via iridium catalysts. This new method of producing chiral compounds was explored for a variety of 1,3-di- and 1,2,4-tri-substituted cyclohexadienes.

  • 3.
    Erdelyi, Mate
    et al.
    Uppsala universitet, Medicinska och farmaceutiska vetenskapsområdet, Farmaceutiska fakulteten, Institutionen för läkemedelskemi. Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Rapid microwave-assisted solid phase peptide synthesis2002Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 11, s. 1592-1596Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A microwave-assisted, rapid solid phase peptide synthesis procedure is presented. It has been applied to the coupling of sterically hindered Fmoc-protected amino acids yielding di- and tripeptides. Optimized conditions for a variety of coupling reagents are reported. Peptides were obtained rapidly (1.5-20 min) and without racemization.

  • 4.
    Johansson, Olof
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för fotokemi och molekylärvetenskap, Molekylär biomimetik.
    Pd-catalyzed amination of chloro-terpyridine for the preparation of amine-containing ruthenium(II) complexes2006Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 15, s. 2585-2589Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The palladium-catalyzed amination reaction of commercially available 4'-chloro-2,2':6',2"-terpyridine opens an easy access to aminated mono- and ditopic terpyridine ligands. The obtained compounds were subsequently used to prepare new amine-containing ruthenium(II) polypyridyl complexes.

  • 5. Mirzaei, Anvar
    et al.
    Biswas, Srijit
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Samec, Joseph
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC, Syntetisk organisk kemi.
    Iron(III)-Catalyzed Nucleophilic Substitution of the Hydroxy Group in Benzoin by Alcohols2012Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 44, nr 8, s. 1213-1218Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The etherification reaction between benzoin derivatives and alcohols catalyzed by iron(III) proceeds in moderate to good yields. Other metal complexes showed either low reactivity or low chemoselectivity where oxidation of benzoin to benzil was a competing reaction. The iron source operated as a catalyst where 5 mol% of iron(III) generate the 2-alkoxy-1,2-diphenylethan-1-one in 50% yield. With an optimum of 25 mol% of catalyst, the desired ether was obtained in 85% yield. The etherification of benzoin and an alcohol proceed to generate the desired product in polar solvents such as 1,2-dichloroethane, whereas less polar solvents promote the competing oxidation to generate the benzil; polar coordinating solvents such as tetrahydrofuran inhibited the reaction. The efficiency of the reaction is found to be dependent on nucleophile where an optimum of 30 equivalents of alcohol was observed. With electron-­donating substituents on the aromatic ring, the etherification was followed by oxidation to generate the benzil. Moderate yields of etherification product were obtained by monitoring the reaction progress with electron-rich substrates and quenching the reaction after two hours.

  • 6.
    Mridha, Moniruzzaman
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - BMC. Mid Sweden Univ, Dept Nat Sci, Holmgatan 10, S-85170 Sundsvall, Sweden..
    Ma, Guangning
    Mid Sweden Univ, Dept Nat Sci, Holmgatan 10, S-85170 Sundsvall, Sweden..
    Palo-Nieto, Carlos
    Mid Sweden Univ, Dept Nat Sci, Holmgatan 10, S-85170 Sundsvall, Sweden..
    Afewerki, Samson
    Mid Sweden Univ, Dept Nat Sci, Holmgatan 10, S-85170 Sundsvall, Sweden.;Stockholm Univ, Arrhenius Lab, Berzelii Ctr EXSELENT, S-10691 Stockholm, Sweden..
    Cordova, Armando
    Mid Sweden Univ, Dept Nat Sci, Holmgatan 10, S-85170 Sundsvall, Sweden.;Stockholm Univ, Arrhenius Lab, Berzelii Ctr EXSELENT, S-10691 Stockholm, Sweden..
    Development of an Amino Acid/Hydroxy Oxime Dual Catalyst System for Highly Stereoselective Direct Asymmetric Aldol Reactions in the Presence of Water2017Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 49, nr 2, s. 383-390Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    An eco-friendly dual catalyst system for stereoselective aldol reactions in the presence of water is described. It is based on the cooperative action of acyclic amino acids and H-bond donating hydroxy oxime catalysts. The synthetic utility of this dual catalyst system was further demonstrated by applying it as the key step in the expeditious and highly stereoselective total synthesis of D-lyxo-phytosphingosine (29% overall yield). Here the amino acid/hydroxy oxime system significantly accelerated the direct aldol reactions in the presence of water as compared to organic solvents. The stereo-and chemoselectivity were also significantly increased.

  • 7. Nilsson, P
    et al.
    Gold, H
    Larhed, M
    Hallberg, A
    Microwave-assisted enantioselective Heck reactions: Expediting high reaction speed and preparative convenience2002Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 11, s. 1611-1614Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Palladium-catalyzed asymmetric Heck reactions have been per-formed using high temperature conditions with the aid of controlled microwave dielectric heating. Significant enantioselectivities of up to 92% ee were obtained under non-inert conditions utilizing the previously reported thermostable palladium-phosphineoxazoline catalytic system. With microwave irradiation. reaction times of hours instead of days were obtained. Enantiomeric purities and conversions were found to be strongly dependent on both the choice of the aryl triflate, the reaction temperature, the solvent and the base. Examples of asymmetric arylations of electron-rich as well as neutral cyclic alkenes are presented.

  • 8.
    Toom, Lauri
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Grennberg, Helena
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Gogoll, Adolf
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Microwave-Assisted Raney Nickel Reduction of Bispidinone Thioketals to N,N’-Dialkylbispidines2006Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 12, s. 2064-2068Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A series of N,N′-dialkyl-3,7-diazabicyclo[3.3.1]nonanes was prepared by microwave-assisted reduction of a common dithiolane precursor with Raney nickel, using the corresponding alkanol as solvent. The method avoids the use of hydrazine.

  • 9. Veiga, Alberte
    et al.
    Arenz, Sven
    Erdelyi, Mate
    N-Arylation of Protected Azamacrocycles2013Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, Vol. 45, nr 6, s. 777-784Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    A rapid method for efficient palladium-catalyzed N-aryl­ation of polynitrogenated macrocycles is presented. Its applicability for functionalization of protected azamacrocycles of various sizes with substituted aryl bromides of optional electronic properties is demonstrated. The compatibility of the protocol with common N-protecting schemes as well as the impact of electronic versus steric factors is discussed. Using a commercially available catalytic system and easily available alkoxide or phenoxide base, the method provides moderate to excellent yields of N-arylated azamacrocycles (45–96%).

  • 10.
    Verendel, J. Johan
    et al.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Church, Tamara L.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi.
    Andersson, Pher G.
    Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för biokemi och organisk kemi, Organisk kemi.
    Catalytic One-Pot Production of Small Organics from Polysaccharides2011Ingår i: Synthesis (Stuttgart), ISSN 0039-7881, E-ISSN 1437-210X, nr 11, s. 1649-1677Artikel, forskningsöversikt (Refereegranskat)
    Abstract [en]

    The catalytic techniques that degrade polysaccharides such as cellulose and elaborate the resulting monomers into organic feedstocks in situ make up an old area of research that has been reignited of late. One-pot conversions of polysaccharides into small organic molecules under acidic, basic, oxidative, reductive and hydrothermal conditions have been reported, and a remarkable breadth of compounds have been produced. 5-Hydroxymethylfurfural (HMF), levulinic acid and polyols such as sorbitol have been obtained in particularly high yields, whereas serious selectivity struggles remain in reactions that produce organic acids such as lactic or glycolic acid. This review covers one-pot, catalytic transformations of polysaccharides into small organic molecules and focuses on mechanism, selectivity and optimization.

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