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Paper | Special issue | Vol 52, No. 2, 2000, pp.603-619
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S45
Diastereoselective Synthesis of α-Butadienyl-β-lactams and Some Stereochemical Aspects of Their Diels-Alder Adducts

Arun K. Sharma, R. Senthil Kumar, and Mohinder P. Mahajan*

*Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar 143005, Punjab, India

Abstract

An efficient diastereoselective synthesis of α-dienyl-β-lactams via [2+2] cycloadditions of imines with butadienyl ketene is reported. The dienyl functionality of α-dienyl-β-lactams was then exploited in Diels-Alder reactions with N-phenylmaleimide (NPM), diethyl fumarate (DEF), ethyl acrylate (EA), 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) and stereochemical aspects of their Diels-Alder adducts are reported.