A Regio and Diastereoselective Bromolactamization of d,g-Unsaturaterd Thioimidates

1 January 1987

journal article
research article
Published by CLOCKSS Archive in HETEROCYCLES

Vol. 26 (2) , 359-362
https://doi.org/10.3987/r-1987-02-0359

Abstract

Cyclization of N-substituted E-.delta.,.gamma.-unsaturated thioimidates (5a-f) with bis(collidine)bromonium perchlorate, followed by treatment with aqueous sodium carbonate afforded the corresponding N-substituted threo-2-(2''-bromoalkyl)pyrrolidin-5-ones (10a-f), respectively, with high diastereoselectivity. Cyclization of Z-unsaturated thioimidate (9) gave the erythroisomer (12).

Keywords

HETEROCYCLES

This publication has 1 reference indexed in Scilit:

Synthesis of .beta.-lactam antibiotics by the sulfeno-cycloamination
Journal of the American Chemical Society, 1983