Stereoselective Glycosylation Reactions with Chiral Auxiliaries

Abstract

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). Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2005/z461745_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.