Halide Effects on Cyclopropenium Cation Promoted Glycosylation with Deoxy Sugars: Highly α??Selective Glycosylations Using a 3, 3??Dibromo??1, 2?? …

…, JP Issa, AHA Chu, JA Sisel, RS Schum…

Index: Nogueira, Jason M.; Issa, John Paul; Chu, An-Hsiang Adam; Sisel, Jordan A.; Schum, Ryan S.; Bennett, Clay S. European Journal of Organic Chemistry, 2012 , # 26 p. 4927 - 4930

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Citation Number: 7

Abstract

Abstract A mixture of 3, 3-dibromocyclopropene and TBAI promotes highly α-selective glycosylation reactions (up to> 20: 1) by using deoxy sugar hemiacetal donors. The reaction provides a convenient method for generating highly reactive glycosyl donors in situ from shelf-stable starting materials. Both armed and disarmed sugars undergo the reaction, and selectivity is independent of the configuration of the donor sugar.