Homolytic carbostannylation of alkenes and alkynes with tributylstannyl enolates.
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.
Miura
K
K
Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
Saito
H
H
Fujisawa
N
N
Wang
D
D
Nishikori
H
H
Hosomi
A
A