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Bridging between Organocatalysis and Biocatalysis: Asymmetric Addition of Acetaldehyde to β‐Nitrostyrenes Catalyzed by a Promiscuous Proline‐Based Tautomerase
Author(s) -
Zandvoort Ellen,
Geertsema Edzard M.,
Baas BertJan,
Quax Wim J.,
Poelarends Gerrit J.
Publication year - 2012
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/anie.201107404
Subject(s) - organocatalysis , biocatalysis , acetaldehyde , chemistry , proline , enamine , catalysis , michael reaction , enantioselective synthesis , stereoselectivity , organic chemistry , stereochemistry , amino acid , biochemistry , reaction mechanism , ethanol
Non‐natural beauty : The enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously (i.e., with non‐natural activity) catalyzes the Michael‐type addition of acetaldehyde to nitrostyrene. Catalysis likely proceeds via enamine formation of the amino‐terminal proline residue of 4‐OT with acetaldehyde (see picture), reminiscent of organocatalysis. High stereoselectivity, low catalyst loading, and water as reaction medium characterize this methodology.