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Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes.

ABSTRACT: The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long-standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E.?meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93?% conversion, excellent selectivity (>99?% ee, >95?% regioselectivity), and on a preparative scale.

SUBMITTER: Demming RM

PROVIDER: S-EPMC6471033 | biostudies-literature | 2019 Jan

REPOSITORIES: biostudies-literature

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Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes.

Demming Rebecca M RM Hammer Stephan C SC Nestl Bettina M BM Gergel Sebastian S Fademrecht Silvia S Pleiss Jürgen J Hauer Bernhard B

Angewandte Chemie (International ed. in English) 20181130 1

The direct enantioselective addition of water to unactivated alkenes could simplify the synthesis of chiral alcohols and solve a long-standing challenge in catalysis. Here we report that an engineered fatty acid hydratase can catalyze the asymmetric hydration of various terminal and internal alkenes. In the presence of a carboxylic acid decoy molecule for activation of the oleate hydratase from E. meningoseptica, asymmetric hydration of unactivated alkenes was achieved with up to 93 % conversion ...[more]

PMID: 30256501

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