193006-89-2Relevant academic research and scientific papers
Enantioselective Synthesis of Chiral 3-Substituted-3-silylpropionic Esters via Rhodium/Bisphosphine-Thiourea-Catalyzed Asymmetric Hydrogenation
Zhang, Zongpeng,Han, Zhengyu,Gu, Guoxian,Dong, Xiu-Qin,Zhang, Xumu
, p. 2585 - 2589 (2017/08/16)
We have successfully developed the asymmetric hydrogenation of β-silyl-α,β-unsaturated esters to prepare chiral 3-substituted-3-silylpropionic ester products catalyzed by rhodium/bisphosphine-thiourea (ZhaoPhos) with excellent results (up to 97% yield, >99% ee, 1500 TON). Moreover, our hydrogenation products can be efficiently converted to other important organic molecules, such as chiral ethyl (R)-3-hydroxy-3-phenylpropanoate or (R)-3-[dimethyl(phenyl)silyl]-3-phenylpropanoic acid. (Figure presented.).
Iridium-Catalyzed Enantioselective Hydrogenation of Vinylsilanes
Wang, Aie,Bernasconi, Maurizio,Pfaltz, Andreas
supporting information, p. 2523 - 2529 (2017/08/16)
We have screened a diverse array of iridium complexes derived from chiral N,P ligands as catalysts for the asymmetric hydrogenation of vinylsilanes, a transformation for which generally applicable catalysts were lacking. Several catalysts emerged from thi
Copper(II)-catalyzed silylation of activated alkynes in water: Diastereodivergent access to E- or Z-β-silyl-α,β-unsaturated carbonyl and carboxyl compounds
Calderone, Joseph A.,Santos, Webster L.
supporting information, p. 4154 - 4158 (2014/05/06)
Copper(II)-catalyzed silylation of substituted alkynylcarbonyl compounds was investigated. Through the activation of Me2PhSiBpin in water at room temperature and open atmosphere, vinylsilanes conjugated to carbonyl groups are synthesized in high yield. A surprising diastereodivergent access to olefin geometry was discovered using a silyl conjugate addition strategy: aldehydes and ketones were Z selective while esters and amides were exclusively transformed into the E products. Dial a diastereomer: The title reaction proceeds through the activation of Me2PhSiBpin in water at room temperature and open atmosphere to produce high yields of vinylsilanes conjugated to carbonyl groups. A surprising diastereodivergent access to olefin geometry was discovered using this silyl conjugate addition strategy: aldehydes were Z selective while esters and amides exclusively delivered the E-configured products.
Synthesis of multi-substituted vinylsilanes via copper(i)-catalyzed hydrosilylation reactions of allenes and propiolate derivatives with silylboronates
Xu, Yun-He,Wu, Liu-Hai,Wang, Jun,Loh, Teck-Peng
supporting information, p. 7195 - 7197 (2014/07/07)
An efficient and general copper(i)-catalyzed method for the synthesis of multi-substituted vinylsilanes is reported. Multi-substituted allenes with electron-withdrawing groups and propiolate derivatives reacted well with (dimethylphenylsilyl)boronic acid
Activation of Si-Si bonds for copper(I)-catalyzed conjugate silylation
Iannazzo, Laura,Molander, Gary A.
, p. 4923 - 4926,4 (2020/08/24)
Several alkyl- and vinylsilanes were prepared through the copper(I)-catalyzed conjugate silylation of α,β-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poo
Enantioselective synthesis of allylsilanes bearing tertiary and quaternary si-substituted carbons through Cu-catalyzed allylic alkylations with alkylzinc and arylzinc reagents
Kacprzynski, Monica A.,May, Tricia L.,Kazane, Stephanie A.,Hoveyda, Amir H.
, p. 4554 - 4558 (2008/09/17)
All sorts of allylsilanes including, for the first time, those that contain a Si-bonded quaternary carbon, were synthesized through efficient and highly enantioselective Cu-catalyzed asymmetric allylic alkylations. Reactions may involve dialkyl- as well as diarylzinc reagents and are promoted by various chiral N-heterocyclic carbene complexes.
A conjugate reduction pathway to chiral silanes using CuH
Lipshutz, Bruce H.,Lee, Ching-Tien,Taft, Benjamin R.
, p. 3257 - 3260 (2008/09/19)
Experimental details concerning asymmetric 1,4-reduction of β-silylated-β,β-disubstituted enoates catalyzed by CuH are described. High yields and enantiomeric excesses are to be expected when Solvias' JOSIPHOS bis-phosphine PPF-P(t-Bu)2 is used as a non-racemic ligand. Georg Thieme Verlag Stuttgart.
Chiral silanes via asymmetric hydrosilylation with catalytic CuH
Lipshutz, Bruce H.,Tanaka, Naoki,Taft, Benjamin R.,Lee, Ching-Tien
, p. 1963 - 1966 (2007/10/03)
CuH-catalyzed asymmetric conjugate reduction of β-silyl-α, β-unsaturated esters has been developed. Using PMHS as a stoichiometric source of hydride and in situ generated CuH ligated by Solvias' JOSIPHOS analogue PPF-P(t-Bu)2 leads to highly enantioselective 1,4-reductions.
Highly stereoselective syntheses of alkenylsilanes and germanes utilizing cyclobutyl ketones
Fujiwara, Tooru,Sawabe, Koichi,Takeda, Takeshi
, p. 8349 - 8370 (2007/10/03)
(E)-Alkenylsilanes were synthesized with high stereoselectivity by the diastereoselective addition of the dimethylphenylsilyllithium to the trans-2-phenylthiocyclobutyl ketones and the Lewis acid-promoted promoted stereospecific ring opening reactions of the resulting cyclobutanemethanol derivatives. (E)-1,5-Disubstituted 1,5-dienylsilanes and germanes were also produced stereoselectively by the similar zinc salt-catalyzed ring opening reaction of α-dimethylphenylsilyl- or α-triethylgermyl-1-[2-(trimethylsilylmethyl)cyclobutane]methanol derivatives.
