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Enantioselective Michael Addition of Water
Author(s) -
Chen BiShuang,
Resch Verena,
Otten Linda G.,
Hanefeld Ulf
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201405579
Subject(s) - enantioselective synthesis , michael reaction , nucleophile , chemistry , organic chemistry , solvent , deuterium , catalysis , physics , quantum mechanics
The enantioselective Michael addition using water as both nucleophile and solvent has to date proved beyond the ability of synthetic chemists. Herein, the direct, enantioselective Michael addition of water in water to prepare important β‐hydroxy carbonyl compounds using whole cells of Rhodococcus strains is described. Good yields and excellent enantioselectivities were achieved with this method. Deuterium labeling studies demonstrate that a Michael hydratase catalyzes the water addition exclusively with anti ‐stereochemistry.