Homolytic carbostannylation of alkenes and alkynes with tributylstannyl enolates

被引：21

作者：

Miura, K ^{[1
]}

Saito, H ^{[1
]}

Fujisawa, N ^{[1
]}

Wang, D ^{[1
]}

Nishikori, H ^{[1
]}

Hosomi, A ^{[1
]}

机构：

[1] Univ Tsukuba, Grad Sch Pure & Appl Sci, Dept Chem, Tsukuba, Ibaraki 3058571, Japan

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 25期

关键词：

D O I：

10.1021/ol016797w

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] 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 alpha -tributylstannylmethyl-gamma -ketoesters, unlike the known Michael-type reaction of stannyl enolates forming delta -ketoesters. The carbostannylation of alkynes proceeded in an anti addition mode to afford beta,gamma -unsaturated ketones. The reactivity of stannyl enolates as radical transfer agents could be utilized for radical cyclization of 1,6-enynes.

引用

页码：4055 / 4057

页数：3

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