147328-49-2Relevant academic research and scientific papers
Fluoride Anions in Self-Assembled Chiral Cage for the Enantioselective Protonation of Silyl Enol Ethers
Paladhi, Sushovan,Liu, Yidong,Kumar, B. Senthil,Jung, Min-Jung,Park, Sang Yeon,Yan, Hailong,Song, Choong Eui
supporting information, p. 3279 - 3282 (2017/06/23)
The potential of Song's chiral oligoethylene glycols (oligoEGs) as catalysts was explored in the enantioselective protonation of trimethylsilyl enol ethers in combination with alkali metal fluoride (KF and CsF) and in the presence of a proton source. Highly enantioselective protonations of various silyl enol ethers of α-substituted tetralones were achieved, producing chiral α-substituted tetralones in full conversion and with up to 99% ee. The established protocol was successfully extended to the synthesis of biologically relevant chiral α-substituted chromanone and thiochromanone derivatives.
Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
Aikawa, Haruo,Kaneko, Tetsuro,Asao, Naoki,Yamamoto, Yoshinori
scheme or table, p. 648 - 652 (2011/08/03)
Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.
Cinchona alkaloid catalyzed enantioselective fluorination of allyl silanes, silyl enol ethers, and oxindoles
Ishimaru, Takehisa,Shibata, Norio,Horikawa, Takao,Yasuda, Naomi,Nakamura, Shuichi,Toru, Takeshi,Shiro, Motoo
supporting information; experimental part, p. 4157 - 4161 (2009/03/11)
(Chemical Equation Presented) Catalytic variant: Allyl silanes and silyl enol ethers 1 are good substrates for the catalytic highly enantioselective fluorodesilylation using a combination of a biscinchona alkaloid, N-fluorobenzenesulfonimide (NFSI), and base (see scheme). Pharmaceutically attractive 3-aryl-3-fluorooxindoles such as 3 can also be synthesized with high enantioselectivity.
Straightforward organocatalytic enantioselective protonation of silyl enolates by means of cinchona alkaloids and carboxylic acids
Poisson, Thomas,Oudeyer, Sylvain,Dalla, Vincent,Marsais, Francis,Levacher, Vincent
experimental part, p. 2447 - 2450 (2009/04/10)
The combination of cinchona alkaloids and carboxylic acids provides a very simple chiral proton source. By using this system, enantioselective protonation of silyl enolates was achieved affording the corresponding ketones in high yields and in up to 75% e
Organocatalytic enantioselective protonation of silyl enolates mediated by cinchona alkaloids and a latent source of HF
Poisson, Thomas,Dalla, Vincent,Marsais, Francis,Dupas, Georges,Oudeyer, Sylvain,Levacher, Vincent
, p. 7090 - 7093 (2008/09/17)
Hidden benefits: The enantioselective organocatalytic protonation of silyl enolates has been achieved by using readily available cinchona alkaloid catalysts (1) and a latent source of HF that delivers "at will" the active catalytic hydrogen fluoride salt
Investigations on the efficiency of regioselective C-deuteration of Endocyclic enolates
Eames, Jason,Weerasooriya, Neluka,Coumbarides, Gregory S.
, p. 181 - 187 (2007/10/03)
Regioselective C-deuteration of a series of Endocyclic enolates (derived from cyclic aryl ketones) was efficiently achieved by quenching the corresponding "base-free" enolate in the presence of a suitable deuterium source. We discuss the structural nature of the deuterium donor and comment on the use of additives within this deuteration step.
