124193-30-2Relevant academic research and scientific papers
Oxidative C-C bond-forming reaction of electron-rich alkylbenzyl ether with trimethylvinyloxysilane
Ying, Bai-Ping,Trogden, Bridget G.,Kohlman, Daniel T.,Liang, Sidney X.,Xu, Yao-Chang
, p. 1523 - 1526 (2004)
Treatment of an electron-rich benzyl ether with DDQ at ambient temperature followed by addition of a silyl enol ether undergoes a C-C bond-forming reaction to afford 3-alkoxy-3-phenyl-propionyl compound. This is a general reaction and works well with a variety of silyl enol ethers to give carbonyl products in yields ranging from 10 to 85%.
Mesoporous aluminosilicate-catalyzed Mukaiyama aldol reaction of aldehydes and acetals
Ito, Suguru,Tanuma, Kenji,Matsuda, Kohei,Hayashi, Akira,Komai, Hirotomo,Kubota, Yoshihiro,Asami, Masatoshi
, p. 8498 - 8504 (2014/12/11)
A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both aldehydes and acetals with silyl enol ethers or ketene silyl acetals to give the corresponding aldol adducts in moderate to high yields. The remarkable high catalytic activity of Al-MCM-41 over amorphous silica-alumina and aluminum-free mesoporous silicate was observed in the reaction. The solid acid catalyst could be recovered easily by filtration and the recovered catalyst was reusable in the same reactions without a significant loss of catalytic activity.
Intermolecular gold(I)-catalyzed alkyne carboalkoxylation reactions for the multicomponent assembly of β-alkoxy ketones
Schultz, Danielle M.,Babij, Nicholas R.,Wolfe, John P.
supporting information, p. 3451 - 3455 (2013/03/13)
A new gold(I)-catalyzed multicomponent synthesis of β-alkoxy ketones from aldehydes, alcohols, and alkynes is described. This atom economical synthesis was achieved through the use of the gold complex (SPhos)AuNTf 2 as a catalyst, and allows for the preparation of a diverse array of β-alkoxy ketone products. Mechanistic studies illustrate that these reactions proceed via gold(I)-catalyzed hydrolysis of the alkyne to an aryl ketone, which then undergoes an aldol reaction with an oxocarbenium ion generated in situ from the aldehyde and alcohol components.
An alternative approach to direct aldol reaction based on gold-catalyzed methoxyl transfer
Zhang, Moran,Wang, Yunxia,Yang, Yang,Hu, Xiangdong
supporting information; experimental part, p. 981 - 985 (2012/06/30)
A mild and catalyzed alternative to the direct aldol reaction has been developed based on the gold-catalyzed methoxy group transfer from dimethyl acetals to terminal alkynes. Due to the simultaneous activation of the acetals, this aldol approach is only functional for acetals but not aldehydes. A ligand effect from the gold complex has also been observed. Copyright
Mesoporous aluminosilicate-catalyzed Sakurai allylation and Mukaiyama aldol reaction of acetals
Ito, Suguru,Hayashi, Akira,Komai, Hirotomo,Kubota, Yoshihiro,Asami, Masatoshi
experimental part, p. 4243 - 4245 (2010/09/07)
In the presence of a catalytic amount of mesoporous aluminosilicate (Al-MCM-41), both allyltrimethylsilane and silyl enol ether reacted with various acetals under mild reaction conditions to afford the corresponding homoallyl ethers and β-alkoxy ketones,
One-pot enol silane formation-Mukaiyama aldol-type addition to dimethyl acetals mediated by TMSOTf
Downey, C. Wade,Johnson, Miles W.,Tracy, Kathryn J.
, p. 3299 - 3302 (2008/09/19)
(Chemical Equation Presented) Various ketones, esters, amides, and thioesters add in high yield to dimethyl acetals in the presence of silyl trifluoromethanesulfonates and an amine base. Acetals derived from aryl, unsaturated, and aliphatic aldehydes are
Polymer-supported dicyanoketene acetal as a π-acid catalyst: Monothioacetalization and carbon-carbon bond formation of acetals
Tanaka, Nobuyuki,Miura, Tsuyoshi,Masaki, Yukio
, p. 1010 - 1016 (2007/10/03)
Polymeric dicyanoketene acetals (DCKA) were synthesized by copolymerization of styrene and divinylbenzene or ethylene glycol dimethacrylate. These novel polymers could be used successfully as recyclable π-acid catalysts in monothioaCetalization or carbon-carbon bond forming reaction of acetals.
Polymer-supported acid catalyst in the carbon-carbon bond formation of acetals with silylated nucleophiles
Tanaka, Nobuyuki,Masaki, Yukio
, p. 1277 - 1279 (2007/10/03)
Polymeric dicyanoketene acetal (DCKA), which was synthesized by co- polymerization of styrene monomer bearing dicyanoketene acetal functionality and ethylene glycol dimethacrylate, was found to be an effective and recyclable catalyst in the carbon-carbon bond formation of acetals with silylated nucleophiles.
Efficient Activation of Acetals, Aldehydes, and Imines toward Silylated Nucleophiles by the Combined Use of Catalytic Amounts of 2 and TMS-CN under Almost Neutral Conditions
Soga, Tsunehiko,Takenoshita, Haruhiro,Yamada, Masaaki,Mukaiyama, Teruaki
, p. 3122 - 3131 (2007/10/02)
In the presence of catalytic amount of a transition metal compound such as 2, Co(acac)2, or NiCl2, trimethylsilyl cyanide smoothly reacts with acetals to form α-methoxy carbonitriles in good yields.In the coexistence of catalytic amounts of Rh
Effective Activation of Carbonyl and Related Compounds with Phosphonium Salts. The Aldol and Michael Reactions of Carbonyl Compounds with Silyl Nucleophiles and Alkyl Enol Ethers
Mukaiyama, Teruaki,Matsui, Shigekazu,Kashiwagi, Kouichi
, p. 993 - 996 (2007/10/02)
In the presence of a catalytic amount of a phosphonium salt, aldol reaction of silyl enol ethers with aldehydes or acetals and the Michael reaction of silyl enol ethers with α,β-unsaturated ketones or acetals proceed smoothly to afford the corresponding a
