Unknown

Dataset Information

0

Demonstration of redox potential of Metschnikowia koreensis for stereoinversion of secondary alcohols/1,2-diols.

ABSTRACT: The present work reports the Metschnikowia koreensis-catalyzed one-pot deracemization of secondary alcohols/1,2-diols and their derivatives with in vivo cofactor regeneration. Reaction is stereoselective and proceeds with sequential oxidation of (R)-secondary alcohols to the corresponding ketones and the reduction of the ketones to (S)-secondary alcohols. Method is applicable to a repertoire of racemic aryl secondary alcohols and 1,2-diols establishing a wide range of substrate specificity of M. koreensis. This ecofriendly method afforded the product in high yield (88%) and excellent optical purity (>98% ee), minimizing the requirement of multistep reaction and expensive cofactor.

SUBMITTER: Meena VS 

PROVIDER: S-EPMC3921931 | biostudies-literature | 2014

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Demonstration of redox potential of Metschnikowia koreensis for stereoinversion of secondary alcohols/1,2-diols.

Meena Vachan Singh VS   Banoth Linga L   Banerjee U C UC  

BioMed research international 20140127

The present work reports the Metschnikowia koreensis-catalyzed one-pot deracemization of secondary alcohols/1,2-diols and their derivatives with in vivo cofactor regeneration. Reaction is stereoselective and proceeds with sequential oxidation of (R)-secondary alcohols to the corresponding ketones and the reduction of the ketones to (S)-secondary alcohols. Method is applicable to a repertoire of racemic aryl secondary alcohols and 1,2-diols establishing a wide range of substrate specificity of M.  ...[more]