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Enantioselective Michael addition of water
Bi-Shuang Chen1, Verena Resch, Linda G Otten
1Technische Universiteit Delft, Gebouw voor Scheikunde, Afdeling Biotechnologie, Julianalaan 136, 2628 BL Delft (Netherlands).
Abstract:
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.
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