Tetrahedron

Ligand exchange reaction of sulfoxides in organic synthesis: A versatile procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids …

T Satoh, H Unno, Y Mizu, Y Hayashi

文献索引：Satoh, Tsuyoshi; Unno, Hideaki; Mizu, Yasuhiro; Hayashi, Yasumasa Tetrahedron, 1997 , vol. 53, # 23 p. 7843 - 7854

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被引用次数: 23

摘要

A novel two-step procedure for one-carbon homologation of methylesters to esters, thioesters, carboxylic acids and amides is described. Methylesters are reacted with lithium carbanion of chloromethyl phenyl sulfoxide to give α-chloro α-sulfinyl ketones in 70 to 90% yields. Potassium enolate of the α-chloro α-sulfinyl ketone was treated with tert-butyllithium at− 78° C to give alkynolate via alkylidene carbenoid. This intermediate was treated with ...