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Organocatalytic Glycosylation by Using Electron‐Deficient Pyridinium Salts
Author(s) -
Das Somnath,
Pekel Daniel,
Neudörfl JörgM.,
Berkessel Albrecht
Publication year - 2015
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.201503156
Subject(s) - pyridinium , chemistry , glycosyl , glycosylation , catalysis , anomer , silylation , organic chemistry , selectivity , conjugate , combinatorial chemistry , biochemistry , mathematical analysis , mathematics
A new organocatalytic glycosylation method based on electron‐deficient pyridinium salts is reported. At ambient temperature and catalyst loadings as low as 1 mol %, 2‐deoxyglycosides were formed from benzyl‐ and silyl‐protected glycals and primary or secondary glycosyl acceptors, with excellent yields and anomeric selectivity. Mechanistic investigations point to alcohol–pyridinium conjugates (1,2‐addition products) as key intermediates in the catalytic cycle.