Metal-Free S(N)2 ' Decarboxylative Rearrangement of beta-Keto Esters

[摘要]：Treatment of 2-methoxycarbonyl- (or 3-cyano-)allyl acetoacetates with a tertiary amine or triphenylphosphane afforded alpha-methylene gamma-substituted delta-keto esters (or nitrile) in satisfactory yields. Various bases and nucleophiles were tested to elucidate the mechanism. The results of the study strongly suggest an intermolecular pathway involving a S(N)2'-decarboxylation-S(N)2' cascade.

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