S-alkyl dithioformates as 1,3-dipolarophiles. Generation of C(2)-unsubstituted penems.
S-Alkyl dithioformates, generated by a cycloreversion process, react as 1,3-dipolarophiles with beta-lactam-based azomethine ylids to provide, after (net) elimination of MeSH, C(2)-unsubstituted penems. The overall cycloreversion/cycloaddition sequence was accelerated by microwave irradiation. [reaction: see text]
School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.
Sylvie
S
Sanchez
John H
JH
Bateson
Peter J
PJ
O'Hanlon
Timothy
T
Gallagher