867182-60-3Relevant academic research and scientific papers
Highly regio- and stereo-selective carbometallation reaction of fluorine-containing internal acetylenes with organocopper reagents
Konno, Tsutomu,Daitoh, Takeshi,Noiri, Atsushi,Chae, Jungha,Ishihara, Takashi,Yamanaka, Hiroki
, p. 9391 - 9404 (2007/10/03)
The carbometallation reactions of fluoroalkylated internal alkynes with various organocopper reagents derived from organolithium, Grignard, and organozinc reagents were examined. All carbocupration reactions proceeded smoothly in a highly regio- and stereo-selective manner to give the corresponding vinylcopper intermediates. The intermediates reacted with H + smoothly, leading to the trisubstituted alkenes in high to excellent yields, whereas they reacted only with strictly limited carbon electrophiles such as allyl-, crotyl-, methallyl bromide, etc, probably due to the low reactivity exerted by an electron-withdrawing fluoroalkyl group. Treatment of vinylcopper with iodine resulted in a high yield of the corresponding vinyl iodide, which was employed successfully for Suzuki-Miyaura and Sonogashira cross-coupling reactions. In addition, two key reactions, the carbocupration and the Suzuki-Miyaura cross-coupling reaction realized the first highly stereoselective total synthesis of anti-estrogen drug, panomifene.
A highly regio- and stereoselective carbocupration of fluoroalkylated internal alkynes: A short total synthesis of the antiestrogenic drug panomifene
Konno, Tsutomu,Daitoh, Takeshi,Noiri, Atsushi,Chae, Jungha,Ishihara, Takashi,Yamanaka, Hiroki
, p. 933 - 936 (2007/10/03)
(Equation presented) A highly regio- and stereoselective carbometalation reaction of fluoroalkylated internal alkynes with organocopper reagents is described. This reaction is utilized successfully in the short, stereoselective total synthesis of the antiestrogenic drug panomifene.
