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).
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Kim et al. (2005) studied this question.
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