doi: 10.1002/anie.201600142.
Epub 2016 May 31.
Stereoselective Koenigs-Knorr Glycosylation Catalyzed by Urea
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- PMID: 27244701
- DOI: 10.1002/anie.201600142
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Stereoselective Koenigs-Knorr Glycosylation Catalyzed by Urea
Angew Chem Int Ed Engl.
.
Abstract
A stereoselective Koenigs-Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea-mediated hydrogen-bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low α-stereoselectivity of glycosylations observed when using perbenzylated glucosyl donors can be greatly improved by the addition of tri-(2,4,6-trimethoxyphenyl)phosphine (TTMPP).
Keywords: carbohydrates; glycosylation; organocatalysis; stereoselectivity; urea.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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