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Stereoselective Glycosylation Reactions with Chiral Auxiliaries
Author(s) -
Kim JinHwan,
Yang Hai,
Boons GeertJan
Publication year - 2005
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.200461745
Subject(s) - glycosylation , stereoselectivity , anomer , activator (genetics) , chemistry , scheme (mathematics) , stereochemistry , combinatorial chemistry , computer science , organic chemistry , catalysis , mathematics , gene , biochemistry , mathematical analysis
Good neighbors : A chiral auxiliary is used for the first time to control the anomeric selectivity of glycosylation reactions. In this approach, upon treatment with an activator A + , neighboring‐group participation of an ( S )‐ethoxycarbonylbenzyl auxiliary at C2 leads to the formation of 1,2‐ cis glycosides, probably via a trans ‐fused ethyloxonium ion intermediate (see scheme).