604010-57-3Relevant academic research and scientific papers
Anti-selective vicinal silaboration and diboration of alkynoates through phosphine organocatalysis
Nagao, Kazunori,Ohmiya, Hirohisa,Sawamura, Masaya
, p. 1304 - 1307 (2015)
Trialkylphosphine organocatalysts have enabled anti-selective vicinal silaboration and diboration of the C-C triple bond in alkynoates to produce β-boryl-α-silyl acrylates and α,β-diboryl acrylates, respectively. The anti stereoselectivity was complete and robust. A variety of functional groups were tolerated in the alkynoates. The two vicinally installed heteroatom substituents of the β-boryl-α-silyl acrylates and α,β-diboryl acrylates could be differentiated and transformed in a stepwise manner, allowing the synthesis of a diverse array of unsymmetrical tetrasubstituted alkenes.
Oxidative heck arylation for the stereoselective synthesis of tetrasubstituted olefins using nitroxides as oxidants
He, Zhiheng,Kirchberg, Sylvia,Froehlich, Roland,Studer, Armido
, p. 3699 - 3702 (2012/05/20)
One, two, and three! Nitroxides and dioxygen serve as oxidants in highly stereoselective oxidative Pd-catalyzed Heck arylations in which aryl boronic acids are used to synthesize triarylalkyl-substituted olefins. The reactions occur under very mild conditions at room temperature. As an example, the threefold sequential arylation of methyl acrylate is the crucial step in the stereoselective synthesis of Z-Tamoxifen.
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.
(Z)-tamoxifen and tetrasubstituted alkenes and dienes via a regio- and stereospecific three-component magnesium carbometalation palladium(O) cross-coupling strategy
Tessier, Pierre E.,Penwell, Andrea J.,Souza, Fabio E. S.,Fallis, Alex G.
, p. 2989 - 2992 (2007/10/03)
(Matrix presented) The synthesis of various tetrasubstituted alkenes and dienes in a regio- and stereocontrolled manner is described. This three-component coupling strategy involves the addition of Grignard reagents to propargyl alcohols followed by palladium(O)-mediated cross-coupling with aryl or vinyl halides. This protocol has been applied to the synthesis of (Z)-Tamoxifen and related mimics.
