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Vinyl sulphones derived from thioglycosides: Synthesis and alkylation

Authors
Journal
Tetrahedron Letters
0040-4039
Publisher
Elsevier
Publication Date
Volume
27
Issue
36
Identifiers
DOI: 10.1016/s0040-4039(00)94273-4

Abstract

Abstract Vinyl sulphones (1-sulphonyl glycals) are formed in good yield by elimination of propanone from 2,3- O -isopropylidene derivatives of D -mannopyranosyl and L -rhanmopyranosyl sulphones. Attempted conjugate addition of carbon nucleophiles to these vinyl sulphones, which are deactivated towards nucleophiles by the ring oxygen atom, was unsuccessful but lithiatlon followed by methylation yielded the 2-methyl vinyl sulphone derivatives when t-butyl sulphones rather than phenyl sulphones were used.

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