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Catalytic Enantioselective Retro‐Aldol Reactions: Kinetic Resolution of β ‐Hydroxyketones with Aldolase Antibodies
Author(s) -
Zhong Guofu,
Shabat Doron,
List Benjamin,
Anderson James,
Sinha Subhash C.,
Lerner Richard A.,
Barbas III Carlos F.
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19981002)37:18<2481::aid-anie2481>3.0.co;2-t
Subject(s) - aldol reaction , aldolase a , enantioselective synthesis , chemistry , kinetic resolution , catalysis , enantiomer , fructose bisphosphate aldolase , antibody , stereochemistry , enzyme , organic chemistry , biology , immunology
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.