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Manifestation of Felkin–Anh Control in Enantioselective Acyl Transfer Catalysis: Kinetic Resolution of Carboxylic Acids
Author(s) -
Yang Xing,
Liu Peng,
Houk K. N.,
Birman Vladimir B.
Publication year - 2012
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.201203327
Subject(s) - enantioselective synthesis , acylation , chemistry , kinetic resolution , organic chemistry , stereochemistry , catalysis , computational chemistry , psychology
Under control: The classical polar Felkin–Anh model has been applied for the first time to the analysis of diastereoselectivity in acylation reactions (see scheme). Computational studies demonstrate that stereoelectronic effects control the enantioselectivity in asymmetric catalytic alcoholysis of acyclic anhydrides.