Homolytic Carbostannylation of Alkenes and Alkynes with Tributylstannyl Enolates

K Miura, H Saito, N Fujisawa, D Wang, H Nishikori…

Index: Miura, Katsukiyo; Saito, Hiroshi; Fujisawa, Naoki; Wang, Di; Nishikori, Hisashi; Hosomi, Akira Organic Letters, 2001 , vol. 3, # 25 p. 4055 - 4057

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Citation Number: 20

Abstract

In the presence of AIBN, tributylstannyl enolates derived from aromatic ketones reacted with electron-deficient alkenes and a variety of alkynes to give the corresponding carbostannylated adducts. The reactions with methyl acrylate gave α-tributylstannylmethyl-γ- ketoesters, unlike the known Michael-type reaction of stannyl enolates forming δ-ketoesters. The carbostannylation of alkynes proceeded in an anti addition mode to afford β, γ- ...