Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 18, Issue 21, Pages 6507-6513Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201104073
Keywords
asymmetric synthesis; heterocyclic compounds; homogeneous catalysis; hydrogenation; iridium
Categories
Funding
- Energi-myndigheten (The Swedish Energy Agency)
- Nordic Energy Research (N-INNER II)
- The Swedish Research Council (VR)
- The Knut and Alice Wallenberg Foundation
- VR/SIDA
- The Anders Jahres Foundation
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available