Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone

Article abstract of DOI:10.1021/jo00124a008

Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity.Di- and trisubstituted olefin derivatives are available through this procedure.Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization.The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring.This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.