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Stereoselective Koenigs–Knorr Glycosylation Catalyzed by Urea
Author(s) -
Sun Lifeng,
Wu Xiaowei,
Xiong DeCai,
Ye XinShan
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201600142
Subject(s) - stereoselectivity , glycosylation , chemistry , glycosyl , catalysis , urea , anomer , phosphine , selectivity , organic chemistry , medicinal chemistry , biochemistry
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).