2 research outputs found
Induced Axial Chirality in Biocatalytic Asymmetric Ketone Reduction
Catalytic asymmetric reduction of prochiral ketones of
type 4-alkylidene
cyclohexanone with formation of the corresponding axially chiral <i>R</i>-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 (<i>S</i>)). Utilization of ketone with a vinyl bromide moiety allows respective <i>R</i>- and <i>S</i>-alcohols to be exploited as key
compounds in Pd-catalyzed cascade reactions
Biocatalytic Route to Chiral Acyloins: P450-Catalyzed Regio- and Enantioselective α‑Hydroxylation of Ketones
P450-BM3
and mutants of this monooxygenase generated by directed
evolution are excellent catalysts for the oxidative α-hydroxylation
of ketones with formation of chiral acyloins with high regioselectivity
(up to 99%) and enantioselectivity (up to 99% ee). This constitutes
a new route to a class of chiral compounds that are useful intermediates
in the synthesis of many kinds of biologically active compounds