Induced Axial Chirality in Biocatalytic Asymmetric Ketone Reduction
Journal of the American Chemical Society2012Vol. 135(5), pp. 1665–1668
Citations Over TimeTop 16% of 2012 papers
Abstract
Catalytic asymmetric reduction of prochiral ketones of type 4-alkylidene cyclohexanone with formation of the corresponding axially chiral R-configurated alcohols (up to 99% ee) was achieved using alcohol dehydrogenases, whereas chiral transition-metal catalysts fail. Reversal of enantioselectivity proved to be possible by directed evolution based on saturation mutagenesis (up to 98% ee (S)). Utilization of ketone with a vinyl bromide moiety allows respective R- and S-alcohols to be exploited as key compounds in Pd-catalyzed cascade reactions.
Related Papers
- → Stereospecific allylsilane reactions: a total synthesis of dihydronepetalactone(1984)43 cited
- → Reactions of organic peroxides. Part XV. Conversion of cyclohexanone into hexan-6-olide(1969)9 cited
- Recent research progress in synthesis of Cyclohexanol and Cyclohexanone from Cyclohexane by Selective Oxidation Process(2009)
- → Behavior of Acrylamide in the Presence of Cyclohexanone and Methyl Ethyl Ketone(1998)1 cited
- → RESEARCHES ON THE POLYVINYL CHLORIDE FIBER(1956)