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Communication | Regular issue | Vol 26, No. 2, 1987, pp.359-362
Published online, 1st January, 1970
DOI: 10.3987/R-1987-02-0359
A Regio and Diastereoselective Bromolactamization of δ,γ-Unsaturaterd Thioimidates

Shinzo Kano, Tsutomu Yokomatsu, Haruo Iwasawa, and Shiroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Cyclization of N-substituted E-δ,γ-unsaturated thioimidates (5a-f) with bis(collidine)bromonium perchlorate, followed by treatment with aqueous sodium carbonate afforded the corresponding N-substituted threo-2- (2’-bromoalky1)pyrrolidin-5-ones (10a-f), respectively, with high diastereoselectivity. Cyclization of Z-unsaturated thioimidate (9) gave the erythro isomer (12).