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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Enantiomerically pure alcohols, as key intermediates, play an essential role in the pharmaceutical, agrochemical and chemical industries.

The use of water as a nucleophile for Michael additions is still a challenge in organic chemistry. In this report we describe the use of amino acids as catalysts for the Michael addition of water to α,β‐unsaturated ketones. All 20 proteinogenic amino acids were screened and L‐lysine was identified as the best candidate. To obtain a better insight and to determine the minimum requirements of the catalyst, several structurally related compounds were tested. The reaction was characterized in terms of conditions and equilibrium.