Abstract
Reaction of the glyoxal diimine 1a with lithium ester enolates 2a-b gave 4-imino-2-azetidinones 3a-c in excellent yields. The biacetyl diimine 1b only reacted with the enolate 2a to yield the 4-imino-2-azetidinone 3d and the 5-methylene-2-pyrrolinone 8 depending on the experimental conditions. In addition, various reactions of compounds 3 and of some derivatives, including two new examples of intramolecular β-lactam ring-opening, are described and discussed.
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