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  • 1.
    Cadu, Alban
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Development of iridium-catalyzed asymmetric hydrogenation: New catalysts, new substrate scope2012In: Journal of Organometallic Chemistry, ISSN 0022-328X, E-ISSN 1872-8561, Vol. 714, p. 3-11Article, review/survey (Refereed)
    Abstract [en]

    A review. The asym. hydrogenation of olefins is a tremendously powerful tool used to synthesize chiral mols. The field was pioneered using rhodium- and ruthenium- based catalysts; however, catalysts based on both of these metals suffer from limitations, such as the need for directing substituents near or even adjacent to the olefin. Iridium-based catalysts do not suffer from this flaw and can thus hydrogenate a wide variety of olefins, including some tetra substituted ones. It is also possible for iridium-based catalysts to hydrogenate hetero-π bonds such as those found in heteroarom. rings. This review summarizes the contributions made to this field by the authors in the past few years. [on SciFinder(R)]

  • 2. Chakka, Sai Kumar
    et al.
    Andersson, Pher G
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
    Maguire, Glenn E. M.
    Kruger, Hendrik G.
    Govender, Thavendran
    Synthesis and Screening of C-1-Substituted Tetrahydroisoquinoline Derivatives for Asymmetric Transfer Hydrogenation Reactions2010In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 5, p. 972-980Article in journal (Refereed)
    Abstract [en]

    Tetrahydroisoquinoline (TIQ) derivatives exhibit good biological activity. However, utilization of TIQ compounds in asymmetric catalysis is limited. This paper presents a series of TIQ derivatives in asymmetric transfer hydrogenation (ATH) reactions. Chiral TIQ amino alcohol ligands were synthesized and screened for the ATH reaction of aromatic ketones. The effect of a cis- and trans-phenyl substitution at the C-1 position on the ligand backbone was investigated both experimentally and computationally. The results showed that the trans orientation on the TIQ scaffold yields higher turnover rates with a selectivity of 94% ee obtained at room temperature with an Ru complex. The cis isomer results in a high turnover rate with no selectivity. The trans isomer gave 99% ee at lower temperatures. Furthermore, it was observed that substitution at the C-3-alpha position results in a drop of the enantioselectivity and the reactivity of the catalyst.

  • 3.
    Verendel, J. Johan
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Li, Jia-Qi
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Quan, Xu
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Peters, Byron
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Zhou, Taigang
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Gautun, Odd R.
    Govender, Thavendran
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes2012In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 21, p. 6507-6513Article in journal (Refereed)
    Abstract [en]

    Several types of chiral hetero- and carbocyclic compounds have been synthesized by using the asymmetric hydrogenation of cyclic alkenes. N,P-Ligated iridium catalysts reduced six-membered cyclic alkenes with various substituents and heterofunctionality in good to excellent enantioselectivity, whereas the reduction of five-membered cyclic alkenes was generally less selective, giving modest enantiomeric excesses. The stereoselectivity of the hydrogenation depended more strongly on the substrate structure for the five- rather than the six-membered cyclic alkenes. The major enantiomer formed in the reduction of six-membered alkenes could be predicted from a selectivity model and isomeric alkenes had complementary enantioselectivity, giving opposite optical isomers upon hydrogenation. The utility of the reaction was demonstrated by using it as a key step in the preparation of chiral 1,3-cis-cyclohexane carboxylates.

  • 4.
    Verendel, J. Johan
    et al.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Nordlund, Michael
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Andersson, Pher G.
    Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC, Synthetical Organic Chemistry.
    Selective, metal-catalyzed transfer of H2 and CO from polyols to alkenes2013In: ChemSusChem, ISSN 1864-5631, E-ISSN 1864-564X, Vol. 6, no 3, p. 426-429Article in journal (Refereed)
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