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Stereoselective Reactions with Stabilized Carbocations
Author(s) -
Cozzi Pier Giorgio,
Benfatti Fides
Publication year - 2010
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.200905235
Subject(s) - carbocation , lewis acids and bases , chemistry , selectivity , catalysis , stereoselectivity , organic chemistry
Blocking one face : Benzylic carbocations, which are easily generated in situ from alcohols or acetates by Brønsted or Lewis acids, undergo selective facial discrimination in diastereoselective reactions (see scheme; FG=functional group). The A values are responsible for the facial selectivity. Catalytic amounts of various Lewis acids can be employed in discriminating one face of the carbocation.