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Claisen-Type Condensation of Vinylogous Acyl Triflates

2005; American Chemical Society; Volume: 8; Issue: 1 Linguagem: Inglês

10.1021/ol0527781

1523-7060

Shin Kamijo, Gregory B. Dudley,

Oxidative Organic Chemistry Reactions

[reaction: see text] The Claisen-type condensation reaction of cyclic vinylogous carboxylic acid triflates with lithium enolates and their analogues produces acyclic alkynes bearing a 1,3-diketone-type moiety. The present transformation is proposed to proceed via a 1,2-addition of the enolate to the vinylogous acyl triflate, followed by fragmentation of the aldolate intermediate.