846541-57-9Relevant academic research and scientific papers
Palladium-catalyzed fluoride-free cross-coupling of intramolecularly activated alkenylsilanes and alkenylgermanes: Synthesis of tamoxifen as a synthetic application
Matsumoto, Kenji,Shindo, Mitsuru
, p. 642 - 650 (2012/05/04)
We have demonstrated that intramolecular hypercoordination of a carboxylic acid is a powerful activation strategy for the palladium-catalyzed cross-coupling reaction of trialkyl(vinyl)silanes and trialkyl(vinyl)germanes under fluoride-free conditions. Z-β-Trialkylsilyl- and Z-β- trialkylgermylacrylic acids, synthesized stereoselectively by olefination with ynolates, are highly stable and useful reagents for cross-coupling with a variety of aryl iodides to provide tetrasubstituted olefins possessing different carbon substituents in a stereocontrolled and diversity-oriented manner. An application to a stereoselective synthesis of (Z)-tamoxifen is also reported. Copyright
Effective synthesis of tamoxifen using nickel-catalyzed arylative carboxylation
Shimizu, Kazuya,Takimoto, Masanori,Mori, Miwako,Sato, Yoshihiro
, p. 3182 - 3184 (2008/02/13)
Tamoxifen was synthesized using a nickel-catalyzed arylative carboxylation developed by our group. The key compound, tetrasubstituted alkene, was synthesized from disubstituted alkyne using a catalytic amount of Ni(0) and DBU in the presence of Ph2Zn under an atmosphere of carbon dioxide. The reaction proceeded smoothly in a regio- and stereoselective manner, and the resultant tetrasubstituted alkene was converted into tamoxifen. Georg Thieme Verlag Stuttgart.
Intramolecularly activated vinylsilanes: Fluoride-free cross-coupling of (Z)-β-(trialkylsilyl)acrylic acids
Shindo, Mitsuru,Matsumoto, Kenji,Shishido, Kozo
, p. 176 - 178 (2007/10/03)
The fluoride-free palladium-catalyzed cross-coupling reaction of trialkyl(vinyl)silanes activated by the intramolecular pentacoordination of carboxylic acid at the Z-β-position is described.
