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S-Alkyl Dithioformates as 1,3-Dipolarophiles. Generation of C(2)-Unsubstituted Penems

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posted on 05.08.2004, 00:00 by Sylvie Sanchez, John H. Bateson, Peter J. O'Hanlon, Timothy Gallagher
S-Alkyl dithioformates, generated by a cycloreversion process, react as 1,3-dipolarophiles with β-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.