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Frontispiece: Advances in Stereoselective 1,2‐ cis Glycosylation using C‐2 Auxiliaries
Author(s) -
Mensink Rens A.,
Boltje Thomas J.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201787062
Subject(s) - stereoselectivity , sulfonium , glycosylation , chiral auxiliary , monosaccharide , chemistry , stereochemistry , combinatorial chemistry , organic chemistry , enantioselective synthesis , catalysis , biochemistry , salt (chemistry)
This review summarizes the recent emergence of a new strategy for stereoselective glycosylation using a C‐2 chiral auxiliary. The operating principle of this methodology is neighboring group participation of the auxiliary to form a sulfonium ion intermediate. The structure of the auxiliary, the type of protecting groups and stereochemistry of the monosaccharide are important factors that determine the mechanism and selectivity of such reactions. Finally, the application of chiral auxiliaries to oligosaccharide synthesis is discussed. For more information see the Review article by R. A. Mensink and T. J. Boltje on page 17637 ff.