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. 1998 Oct 2;37(18):2481-2484.
doi: 10.1002/(SICI)1521-3773(19981002)37:18<2481::AID-ANIE2481>3.0.CO;2-T.

Catalytic Enantioselective Retro-Aldol Reactions: Kinetic Resolution of β-Hydroxyketones with Aldolase Antibodies

Guofu Zhong  1 , Doron Shabat  1 , Benjamin List  1 , James Anderson  1 , Subhash C Sinha  1 , Richard A Lerner  1 , Carlos F Barbas Iii  1
Affiliations

Catalytic Enantioselective Retro-Aldol Reactions: Kinetic Resolution of β-Hydroxyketones with Aldolase Antibodies

Guofu Zhong et al. Angew Chem Int Ed Engl. .

Abstract

High enantiomeric enrichment after 50% conversion: Racemates of aldols can be resolved by the title reaction [Eq.(1)] by use of the aldolase antibody 38C2 or 33F12; the ee values of the unconverted aldols are greater than 95% in most cases. Since the antibodies also catalyze the aldol reaction-that is, the reverse reaction-it is possible to prepare both enantiomers using the same antibody catalysts.

Keywords: Aldol reactions; Asymmetric synthesis; Catalytic antibodies; Enantiomeric resolution; Retro-aldol reactions.

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