Diastereoselective synthesis of α-butadienyl-β-lactams and some stereochemical aspects of their Diels-Alder adducts

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

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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.

Original languageEnglish (US)
Pages (from-to)603-619
Number of pages17
JournalHeterocycles
Volume52
Issue number2
Publication statusPublished - Feb 1 2000

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All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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