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Communication | Regular issue | Vol 63, No. 5, 2004, pp.1009-1012
Published online, 24th February, 2004
DOI: 10.3987/COM-04-10018
Formation of 3-Pyrrolin-2-ones via 5-Endo-trig Cyclization

Ruri Naitoh, Yayoi Nakamura, Emi Katano, Yohoko Nakamura, Emi Okada, and Morio Asaoka*

*Department of Chemical and Biological Sciences, Faculty of Science, Japan Women’s University, 2-8-1 Mejirodai, Bunkyoku, Tokyo 112-0015, Japan

Abstract

Anionic cyclization of N-benzyl-3-phenylsulfanyl-2-propenamide derivatives gave the corresponding 3-pyrrolin-2-ones. Mechanistic investigation using deuterated starting materials revealed this cyclization proceeds via a 5-endo-trig process.