Tetrahedron Letters p. 4355 - 4358 (1986)
Update date:2022-07-31
Topics:
Cassidy, Joseph F.
Williams, J. Michael
Vinyl sulphones (1-sulfonyl glycals) are formed in good yield by elimination of propanone from 2,3-O-isopropylidene derivatives of D-mannopyranosyl and L-rhamnopyranosyl sulphones.Attempted conjugate addition of carbon nucleophiles to these vinyl sulphones, which are deactivated towards nucleophiles by the ring oxygen atom, was unsuccessful but lithiation followed by methylation yielded the 2-methyl vinyl sulphone derivatives when t-butyl sulphones rather than phenyl sulphones were used.
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(1987)
