119180-85-7Relevant academic research and scientific papers
Access to Enantioenriched Organosilanes from Enals and β-Silyl Enones: Carbene Organocatalysis
Zhang, Yuxia,Huang, Jie,Guo, Yingying,Li, Lin,Fu, Zhenqian,Huang, Wei
supporting information, p. 4594 - 4598 (2018/03/21)
Herein, an efficient route to enantioenriched organosilanes, containing two consecutive stereogenic centers, from enals and β-silyl enones under carbene organocatalysis is described. Under mild reaction conditions, this transition-metal-free strategy exhibits a broad substrate scope, and excellent diastereo- and enantioselectivity.
Cyclopropanation of strained alkenes by palladium-catalyzed reaction of 3-trimethylsilyl- or 3-pinacolatoboryl-1-arylallyl acetates
Horino, Yoshikazu,Homura, Naoki,Inoue, Kana,Yoshikawa, Saori
supporting information; experimental part, p. 828 - 834 (2012/05/04)
The palladium-catalyzed cyclopropanation of strained alkenes with 3-trimethylsilyl- or 3-pinacolatoboryl-1-arylallyl acetate derivatives is described. This reaction gives cyclopropanation products in good to high yields with a single diastereomer, and the key step is likely to involve the formation of a palladacyclobutene complex from the α-trimethylsilyl- or α-pinacolatoboryl-σ-allylpalladium complex. Copyright
Studies on retro-[1,4] Brook rearrangement of 3-silyl allyloxysilanes. Observation of the formation of unusual 3,3-bissilyl enols
Gan, Zubao,Wu, Ya,Gao, Lu,Sun, Xianwei,Lei, Jian,Song, Zhenlei,Li, Linjie
supporting information; experimental part, p. 6928 - 6934 (2012/08/29)
Detailed investigations of the retro-[1,4] Brook rearrangement of 3-silyl allyloxysilanes are described. Based on control experiments and NMR studies, rationalizations are proposed for the formation of 3,3-bissilyl enols, unusual compounds that are stable
Novel sequential 1,4-Brook rearrangement-Wittig reaction: New one-pot approach for silyl dienol ethers
Matsuya, Yuji,Koiwai, Azusa,Minato, Daishiro,Sugimoto, Kenji,Toyooka, Naoki
supporting information, p. 5955 - 5957,3 (2020/07/31)
A novel one-pot synthetic method of silyl dienol ethers via 1,4-Brook rearrangement-Wittig reaction sequence has been developed. This tandem reaction proceeded via the intramolecular silyl migration step, which enabled stereoselective formation of phosphorane intermediates. The reaction is operationally simple and high yielding, thus providing a new useful formula for silyl dienol ether synthesis.
Rhodium(I)-catalyzed [4+1] cycloaddition reactions of α, βunsaturated imines with terminal alkynes for the preparation of pyrrole derivatives
Mizuno, Akio,Kusama, Hiroyuki,Iwasawa, Nobuharu
supporting information; experimental part, p. 8318 - 8320 (2010/02/27)
Rhodium vinylidene intermediates are characteristic for the title reaction (see scheme; coe = cyclooctene, cy = cyclohexyl). This reaction proceeds by the nucleophilic addition of the nitrogen atom of the imine to the rhodium vinylidene complex to give a zwitterionic intermediate, which undergoes intramolecular cyclization to afford the corresponding pyrrole.
[2,3]-Wittig rearrangement of enantiomerically enriched 3-substituted 1-propenyloxy-1-phenyl-2-propen-1-yl carbanions: Effect of heteroatoms and conjugating groups on planarization of an α-oxy-benzylcarbanion through a double bond
Sasaki, Michiko,Ikemoto, Hidaka,Kawahata, Masatoshi,Yamaguchi, Kentaro,Takeda, Kei
supporting information; experimental part, p. 4663 - 4666 (2010/03/03)
The effect of conjugating electron-withdrawing groups and α-anion-stabilizing heteroatom substituents on configurational stability of chiral carbanions through a double bond was examined on the basis of extent of chirality transfer in intramolecular trapp
Cu-catalyzed asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic β-silyl-α,β-unsaturated ketones. Synthesis of allylsilanes in high diastereo- and enantiomeric purity
Kacprzynski, Monica A.,Kazane, Stephanie A.,May, Tricia L.,Hoveyda, Amir H.
, p. 3187 - 3190 (2008/02/11)
A readily available and simple (MW = 444.5 g/mol) valine-based chiral phosphine is used to promote highly efficient catalytic asymmetric conjugate additions of dialkyl- and diarylzinc reagents to acyclic β-silyl-α, β-unsaturated ketones. The catalytic asy
TRANS-3-SILYL ALLYLIC ALCOHOLS VIA THE BROWN VINYLATION
Rane, Anil M.,Vaquer, Jaime,Colberg, Juan C.,Soderquist, John A.
, p. 987 - 990 (2007/10/02)
The addition of representative aldehydes to trans-vinylborane 1 provided pure trans-3-silyl allylic alcohols 2 in excellent yields.The combination of dehydroborylation and insertion leads to the novel dihydroisobenzofuran 7.
A HIGHLY EFFICIENT KINETIC RESOLUTION OF γ- AND β-TRIMETHYLSILYL SECONDARY ALLYLIC ALCOHOLS BY THE SHARPLESS ASYMMETRIC EPOXIDATION
Kitano, Yasunori,Matsumoto, Takashi,Sato, Fumie
, p. 4073 - 4086 (2007/10/02)
Kinetic resolution of γ- and β-trimethylsilyl secondary allylic alcohols proceeds with very large and synthetically satisfactory rate differences for the two enentiomers, respectively, thus providing a convenient and widely applicable method for preparati
1-LITHIO-1-BENZENESULFINYL-2-TRIMETHYLSILYLETHANE AS A 2-TRIMETHYLSILYLVINYL ANION EQUIVALENT IN REACTIONS WITH ALHEDYDES, KETONES AND EPOXIDES
Hsiao, C-N.,Shechter, H.
, p. 2371 - 2374 (2007/10/02)
Aldehydes, ketones and epoxides give adducts with 1-lithio-1-benzenesulfinyl-2-trimethylsilylethane which upon neutralization eliminate benezenesulfenic acid efficiently at 76 deg C to yield trans-3-(trimethylsilyl)allyl alcohols and trans-4-(trimethylsilyl)-3-alken-1-ols.
