- Access to Enantioenriched Organosilanes from Enals and β-Silyl Enones: Carbene Organocatalysis
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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.
- Zhang, Yuxia,Huang, Jie,Guo, Yingying,Li, Lin,Fu, Zhenqian,Huang, Wei
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p. 4594 - 4598
(2018/03/21)
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- Oxidative cross-coupling of vinylsilanes in water
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Palladium-promoted cross-dimerization reaction of alkenylsilanes is reported for the first time, which is also one of the very first studies on oxidative cross-coupling between vinylic organometallic reagents. The reaction occurs at room temperature in aqueous micelles and represents a convenient access to all-trans push-pull butadienes.
- Cicco, Stefania R.,Martinelli, Carmela,Pinto, Vita,Naso, Francesco,Farinola, Gianluca M.
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- Novel sequential 1,4-Brook rearrangement-Wittig reaction: New one-pot approach for silyl dienol ethers
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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.
- Matsuya, Yuji,Koiwai, Azusa,Minato, Daishiro,Sugimoto, Kenji,Toyooka, Naoki
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p. 5955 - 5957,3
(2020/07/31)
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- Rhodium(I)-catalyzed [4+1] cycloaddition reactions of α, βunsaturated imines with terminal alkynes for the preparation of pyrrole derivatives
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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.
- Mizuno, Akio,Kusama, Hiroyuki,Iwasawa, Nobuharu
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supporting information; experimental part
p. 8318 - 8320
(2010/02/27)
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- 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
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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
- Kacprzynski, Monica A.,Kazane, Stephanie A.,May, Tricia L.,Hoveyda, Amir H.
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p. 3187 - 3190
(2008/02/11)
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- Silyl Derivatives in the Synthesis of trans-β-Trimethylsilyl-α,β-unsaturated Ketones
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Methods for the preparation of α-halo-α-(trimethylsilyl)methyl ethers are described.These substances react with (trimethylsilyl)methyl ketones to yield β-methoxy-β-(trimethylsilyl)ethyl ketones.Sodium trimethylsilanoate in dichloromethane solution has bee
- Christiansen, Mette Lene,Benneche, Tore,Undheim, Kjell
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p. 536 - 540
(2007/10/02)
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- Chloro(phenylthio)methyltrimethylsilane: Preparation and some Synthetic Reactions
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Reaction of the title compound (2) with lead thiocyanate gave phenylthio(trimethylsilyl)methyl isothiocyanate (3) which further reacted with aromatic aldehydes in the presence of fluoride ion to afford oxazoles in good yields.Compound (2) also reacted with silyl enol ethers to give β-silyl ketones which were capable of being converted into β-functionalized vinylsilanes.
- Yamamoto, Iwao,Okuda, Kazuhide,Nagai, Shigemasa,Motoyoshiya, Jiro,Gotoh, Haruo,Matsuzaki, Kei
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p. 435 - 438
(2007/10/02)
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