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Direction of Kinetically versus Thermodynamically Controlled Organocatalysis and Its Application in Chemoenzymatic Synthesis
Author(s) -
Rulli Giuseppe,
Duangdee gnaphat,
Baer Katrin,
Hummel Werner,
Berkessel Albrecht,
Gröger Harald
Publication year - 2011
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.201008042
Subject(s) - organocatalysis , enantioselective synthesis , aldol reaction , catalysis , chemistry , control (management) , organic chemistry , combinatorial chemistry , computer science , artificial intelligence
The catalyst loading in the narrow range between 0.5 and 10 mol % determines whether an enantioselective organocatalytic aldol reaction proceeds under kinetic or thermodynamic control; high conversions and ee values can be achieved with low catalyst loadings (see scheme). Since the reaction is carried out in water, it can be combined with a biocatalytic reduction for the one‐pot synthesis of 1,3‐diols with d.r. >25:1 and 99 % ee.