Synlett 2017; 28(12): 1453-1456
DOI: 10.1055/s-0036-1558974
letter
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Synthesis of 3-(5-Benzoyl-1-methyl-1H-pyrrol-2-yl)-2-azetidinone Derivatives via an in Situ Generated Ketene

Behjat Bananezhad, Mohammad Reza Islami*
  • Department of Chemistry, Shahid Bahonar University of Kerman, 76169 Kerman, Iran   Email: mrislami@uk.ac.ir
Further Information

Publication History

Received: 24 December 2016

Accepted after revision: 27 February 2017

Publication Date:
06 April 2017 (eFirst)

Abstract

A short route toward β-lactams from tolmetin has been developed. In the key step, a ketene was generated on the C-2 of pyrrole ring and reacted with aromatic imines to form trans-β-lactams as the only observed products. The identification of the ketene was confirmed by reaction with the stable free radical TEMPO (TO·).

Supporting Information