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