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Mimicry of Polyketide Synthases—Enantioselective 1,4‐Addition Reactions of Malonic Acid Half‐Thioesters to Nitroolefins
Author(s) -
Lubkoll Jana,
Wennemers Helma
Publication year - 2007
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.200702187
Subject(s) - polyketide , enantioselective synthesis , moiety , malonic acid , chemistry , conjugate , michael reaction , stereochemistry , cinchona , organic chemistry , enzyme , biosynthesis , catalysis , mathematical analysis , mathematics
Bifunctionality is the key for mimicking the active site of polyketide synthases with synthetic metal‐free organocatalysts (see picture). Cinchona alkaloid derivatives bearing both a basic site and a urea moiety catalyze conjugate enantioselective addition reactions of malonic acid half thioesters (MAHTs) to nitroolefins with up to quantitative yields and selectivities up to 90 % ee.
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