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.
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Organic Chemistry