Chiral Hetero- and Carbocyclic Compounds from the Asymmetric Hydrogenation of Cyclic Alkenes
2012 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 18, no 21, 6507-6513 p.Article in journal (Refereed) Published
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.
Place, publisher, year, edition, pages
2012. Vol. 18, no 21, 6507-6513 p.
asymmetric synthesis, heterocyclic compounds, homogeneous catalysis, hydrogenation, iridium
Research subject Organic Chemistry
IdentifiersURN: urn:nbn:se:su:diva-119678DOI: 10.1002/chem.201104073OAI: oai:DiVA.org:su-119678DiVA: diva2:847682