In spite of many methods developed for the synthesis of glycans, anomeric halides first employed as glycosyl donors by Michael some 140 years ago continue to find wide application. Under classical Koenigs-Knorr reaction conditions, however, glycosyl halide donors react very slowly. Many modifications of this reaction have emerged, but many still provide low yields or require toxic reagents.<br/> <br/>Inspired by advances in organocatalytic activation of glycosyl halides made by the Ye and the Jacobsen groups, presented herein are our recent investigation of glycosylation reaction with glycosyl halides as donors. These studies led to the discovery of the regenerative glycosylation reaction, Lewis acid-catalyzed Koenigs-Knorr glycosylations, and iron(III)-catalyzed reactions. These studies have also uncovered some unusual reactivity trends among a series of differentially protected glycosyl halides that will also be presented.

Towards catalytic activation of glycosyl halides

2019 Fall National Meeting

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