3-(Prop-2-enylidene)azetidin-2-one derivatives: Synthesis, structure, and formation of 3-spiro-β-lactams via Diels-Alder reactions

Article abstract of DOI:10.1002/hlca.19950780310

Reactions of 3-silylated β-lactams (1) with α,β-unsaturated ketones give the propylidene-β-lactams 3 and the cycloalkenylidene derivatives 5. Structure and configuration are elucidated by spectroscopic methods, and the reactivity is discussed. While compounds 5 do not react with dienophiles, the (Z)-isomers of 3 are the favored substrates for Diels-Alder reactions yielding the spiro compounds 6 and 7.