Enantioselective Michael Addition of Water. Issue 7 (21st December 2014)

• Record Type: Journal Article
• Authors: Chen, Bi‐Shuang; Resch, Verena; Otten, Linda G.; Hanefeld, Ulf
• Is Part Of: Chemistry. Volume 21:Issue 7(2015)
• Page Start: 3020
• Page End: 3030
• Publication Date: 2014-12-21
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201405579
• Languages: English
• ISSNs: 0947-6539

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 <italic>Rhodococcus</italic> 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 <italic>anti</italic>‐stereochemistry.</p> </abstract>