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A New Route to exo ‐Glycals Using the Ramberg−Bäcklund Rearrangement
Author(s) -
Griffin Frank K.,
Paterson Duncan E.,
Murphy Paul V.,
Taylor Richard J. K.
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:7<1305::aid-ejoc1305>3.0.co;2-0
Subject(s) - chemistry , glycosyl , stereochemistry , cellobiose , mannose , galactose , organic chemistry , cellulose , cellulase
Abstract A new route to exo ‐glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg−Bäcklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di‐, tri‐, and tetra‐substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)