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American Chemical Society, Organic Letters, 2(13), p. 284-287, 2010

DOI: 10.1021/ol1027267

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Stereoelectronic Effects Determine Oxacarbenium vs β-Sulfonium Ion Mediated Glycosylations

Journal article published in 2011 by Thomas J. Boltje, Jin-Hwan Kim, Jin Park, Geert-Jan Boons ORCID
This paper is available in a repository.
This paper is available in a repository.

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Abstract

Activation of a glycosyl donor protected with a 2-O-(S)-(phenylthiomethyl)benzyl ether chiral auxiliary results in the formation of an anomeric β-sulfonium ion, which can be displaced with sugar alcohols to give corresponding α-glycosides. Sufficient deactivation of such glycosyl donors by electron-withdrawing protecting groups is, however, critical to avoid glycosylation of an oxacarbenium ion intermediate. The latter type of glycosylation pathway can also be suppressed by installing additional substituents in the chiral auxiliary.