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Asymmetric Enzymatic Hydration of Unactivated, Aliphatic Alkenes
Author(s) -
Demming Rebecca M.,
Hammer Stephan C.,
Nestl Bettina M.,
Gergel Sebastian,
Fademrecht Silvia,
Pleiss Jürgen,
Hauer Bernhard
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810005
Subject(s) - enantioselective synthesis , chemistry , regioselectivity , catalysis , selectivity , enzyme , organic chemistry , alkene , enzyme catalysis , carboxylic acid , combinatorial chemistry
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.