S-alkyl dithioformates as 1,3-dipolarophiles. Generation of C(2)-unsubstituted penems

Sylvie Sanchez; John H Bateson; Peter J O'Hanlon; Timothy Gallagher

doi:10.1021/ol048991z

S-alkyl dithioformates as 1,3-dipolarophiles. Generation of C(2)-unsubstituted penems

Org Lett. 2004 Aug 5;6(16):2781-3. doi: 10.1021/ol048991z.

Authors

Sylvie Sanchez¹, John H Bateson, Peter J O'Hanlon, Timothy Gallagher

Affiliation

¹ School of Chemistry, University of Bristol, Bristol BS8 1TS, UK.

PMID: 15281768
DOI: 10.1021/ol048991z

Abstract

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]