82570-93-2Relevant academic research and scientific papers
Synthesis of Enantioenriched Allylic Silanes via Nickel-Catalyzed Reductive Cross-Coupling
Hofstra, Julie L.,Cherney, Alan H.,Ordner, Ciara M.,Reisman, Sarah E.
supporting information, p. 139 - 142 (2018/01/17)
An asymmetric Ni-catalyzed reductive cross-coupling has been developed to prepare enantioenriched allylic silanes. This enantioselective reductive alkenylation proceeds under mild conditions and exhibits good functional group tolerance. The chiral allylic silanes prepared here undergo a variety of stereospecific transformations, including intramolecular Hosomi-Sakurai reactions, to set vicinal stereogenic centers with excellent transfer of chirality.
Trifluoromethylation of allylsilanes under photoredox catalysis
Mizuta, Satoshi,Engle, Keary M.,Verhoog, Stefan,Galicia-López, Oscar,O'Duill, Miriam,Médebielle, Maurice,Wheelhouse, Katherine,Rassias, Gerasimos,Thompson, Amber L.,Gouverneur, Véronique
supporting information, p. 1250 - 1253 (2013/05/09)
A new catalytic method to access allylic secondary CF3 products is described. These reactions use the visible light excited Ru(bpy) 3Cl2·6H2O catalyst and the Togni or Umemoto reagent as the CF3 source. The photoredox catalytic manifold delivers enantioenriched allylic trifluoromethylated products not accessible under Cu(I) catalysis.
Asymmetric Synthesis Catalyzed by Chiral Ferrocenylphosphine-Transition-Metal Complexes. 3. Preparation of Optically Active Allylsilanes by Palladium-Catalyzed Asymmetric Grignard Cross-Coupling
Hayashi, Tamio,Konishi, Mitsuo,Okamoto, Yasuo,Kabeta, Keiji,Kumada, Makoto
, p. 3772 - 3781 (2007/10/02)
Asymmetric cross-coupling of the - or -Grignard reagent with alkenyl bromides in the presence of a chiral ferrocenylphosphine-palladium complex, dichloroethylamine>palladium(II) (PdCl2), as a catalyst, gave optically active allylsilanes which contain an asymmetric carbon atom directly bonded to the silicon atom, e.g., (R)-3-phenyl-3-(trimethylsilyl)propene (3a) (95percent ee), (R,E)-1-phenyl-1-(trimethylsilyl)-2-butene (3b) (85percent ee), (R,Z)-3b (24percent ee), (R,E)-1,3-diphenyl-3- (trimethylsilyl)propene (3c) (95percent ee), (S,E)-1-phenyl-3-(trimethylsilyl)-1-butene (14c) (71percent ee), (S,Z)-14c (59percent ee), (S,E)-1-phenyl-3-(triethylsilyl)-1-butene (16c) (93percent ee), (S,E)-3-(triethylsilyl)-2-pentene (16b) (85percent ee), (S,E,E)-2-(dimethylphenylsilyl)-3,5-heptadiene (15d) (45percent ee), and 1-cyclopentene (21) (37percent ee).The configuration and enantiomeric purity of the allylsilanes were determined with the aid of stereoselective oxidative cleavage of the carbon-silicon bond in optically active alkylsilanes.
