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Kinetic resolution of secondary alcohols using amidine-based catalysts.

ABSTRACT: Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols and 2-substituted cycloalkanols, and thus provide a viable alternative to enzymes.

SUBMITTER: Li X

PROVIDER: S-EPMC3291098 | biostudies-literature | 2012 Feb

REPOSITORIES: biostudies-literature

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Kinetic resolution of secondary alcohols using amidine-based catalysts.

Li Ximin X Jiang Hui H Uffman Eric W EW Guo Lei L Zhang Yuhua Y Yang Xing X Birman Vladimir B VB

The Journal of organic chemistry 20120209 4

Kinetic resolution of racemic alcohols has been traditionally achieved via enzymatic enantioselective esterification and ester hydrolysis. However, there has long been considerable interest in devising nonenzymatic alternative methods for this transformation. Amidine-based catalysts (ABCs), a new class of enantioselective acyl transfer catalysts developed in our group, have demonstrated, inter alia, high efficacy in the kinetic resolution of benzylic, allylic, and propargylic secondary alcohols ...[more]

PMID: 22283696

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