Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes

Authors

  • J. Johan Verendel,

    1. Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    Search for more papers by this author
  • Jia-Qi Li,

    1. Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    Search for more papers by this author
  • Xu Quan,

    1. Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    Search for more papers by this author
  • Byron Peters,

    1. Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    Search for more papers by this author
  • Taigang Zhou,

    1. Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    Search for more papers by this author
  • Dr. Odd R. Gautun,

    1. Department of Chemistry, Norwegian University of Science and Technology (NTNU), NO-7491, Trondheim (Norway)
    Search for more papers by this author
  • Prof. Thavendran Govender,

    1. School of Chemistry, University of KwaZulu-Natal, Durban, (South Africa)
    Search for more papers by this author
  • Prof. Pher G. Andersson

    Corresponding author
    1. Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    2. School of Chemistry, University of KwaZulu-Natal, Durban, (South Africa)
    • Department of Biochemistry and Organic Chemistry, Uppsala University, Box 576, S-75123, Uppsala (Sweden), Fax: (+46) 18-471-3705
    Search for more papers by this author

Abstract

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.

Ancillary