Konno Tsutomu, Takehana Tsuyoshi, Chae Jungha, Ishihara Takashi, Yamanaka Hiroki
Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-8585, Japan.
J Org Chem. 2004 Mar 19;69(6):2188-90. doi: 10.1021/jo030272v.
Carbostannylation of fluoroalkylated alkynes with various allylstannanes in the presence of AIBN was investigated. In the case of the allylstannane having an electron-withdrawing group at the beta position, the reaction proceeded highly regio- and stereoselectively to give the corresponding allylstannylated products in high yields. Even in the absence of AIBN, the reaction took place smoothly in a highly regio- and stereoselective manner under an atmosphere of air. Thus-obtained vinylstannanes were subjected to the Migita-Kosugi-Stille coupling reaction conditions, affording the tetrasubstituted alkenes in excellent yields.
