Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
作者:Benito Alcaide、Javier Perez-Castells、Concepcion Polanco、Miguel A. Sierra
DOI:10.1021/jo00124a008
日期:1995.9
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.
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