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Novel One-pot Three-component Coupling Reaction with Trimethylsilylmethyl-phosphonate, Acyl Fluoride, and Aldehyde through the Horner-Wadsworth-Emmons Reaction

Taiki Umezawa*, Tomoya Seino and Fuyuhiko Matsuda

*Division of Environmental Materials Science, Graduate School of Environmental Science, Hokkaido University, Sapporo 060-0810, Japan, Email: umezawaees.hokudai.ac.jp

T. Umezawa, T. Seino, F. Matsuda, Org. Lett., 2012, 14, 4206-4209.

DOI: 10.1021/ol301879a (free Supporting Information)


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Abstract

A sequential nucleophilic addition of lithio-trimethylsilylmethylphosphonate to an acyl fluoride followed by generation of a lithio-β-ketophosphonate by desilylation and a Horner-Wadsworth-Emmons reaction of an aldehyde took place cleanly in a one-pot operation. Various E- and Z-enones were obtained in high yields with high stereoselectivities by this one-pot procedure.

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Key Words

enones, Wittig-Horner reaction


ID: J54-Y2012-2600