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Synthesis 2009(21): 3654-3660  
DOI: 10.1055/s-0029-1216997
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Chromatography-Free Enzymatic Kinetic Resolution of Secondary Alcohols

Matthias Maywald, Andreas Pfaltz*
Department of Chemistry, University of Basel, St. Johanns-Ring 19, 4056 Basel, Switzerland
Fax: +41(61)2671103; e-Mail: andreas.pfaltz@unibas.ch;
Further Information

Publication History

Received 18 May 2009
Publication Date:
08 September 2009 (online)

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Abstract

Racemic secondary alcohols were resolved by enzymatic esterification using Candida antarctica lipase B (CAL B). After derivatization of the unreacted enantiomer with phthalic anhydride, the resulting phthalic acid monoesters could be easily separated from the corresponding acetates by precipitation and filtration or distillation, thus avoiding laborious column chromatography, which is a major obstacle for large-scale reactions. This method has been successfully applied to the multigram synthesis of enantiopure pyridyl alcohols.

Key words

alcohols - asymmetric synthesis - enzymes - esterification - kinetic resolution

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