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Control of α/β Stereoselectivity in Lewis Acid Promoted C‐Glycosidations Using a Controlling Anomeric Effect Based on the Conformational Restriction Strategy
Author(s) -
Tamura Satoru,
Abe Hiroshi,
Matsuda Akira,
Shuto Satoshi
Publication year - 2003
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.200390261
Subject(s) - stereoselectivity , anomer , lewis acids and bases , anomeric effect , chemistry , stereochemistry , organic chemistry , catalysis
The kinetic anomeric effect has been used to control both α and β stereoselectivity in glycosidation reactions. Depending on the restricted conformation 4 C 1 or 1 C 4 of the substrate, the anomeric α ( 1 → 2 ) or β product ( 3 → 4 ) was obtained highly stereoselectively from the Lewis acid promoted anomeric allylation with allyltrimethylsilane (TIPS=triisopropylsilyl).