935480-01-6Relevant academic research and scientific papers
Enantioselective Cyanosilylation of α,α-Dialkoxy Ketones by Using Phosphine-Thiourea Dual-Reagent Catalysis
Yu, Qi-Wen,Wu, Lu-Ping,Kang, Tian-Chen,Xie, Jin,Sha, Feng,Wu, Xin-Yan
, p. 3992 - 3996 (2018/07/31)
The first highly enantioselective cyanosilylation of α,α-dialkoxy ketones enabled by a dual-reagent catalysis has been developed. With the combination of a chiral bifunctional phosphine-thiourea and methyl acrylate, the key organophosphorus zwitterion intermediate was generated in situ as a novel Lewis base, which catalyzed the enantioselective cyanosilylation reaction in excellent yields (up to 99 %) with good-to-excellent enantioselectivities (up to 94 % ee).
Enantioselective cyanosilylation of α,α-dialkoxy ketones catalyzed by proline-derived in-situ-prepared N-oxide as bifunctional organocatalyst
Qin, Bo,Liu, Xiaohua,Shi, Jian,Zheng, Ke,Zhao, Haitao,Feng, Xiaoming
, p. 2374 - 2378 (2007/10/03)
Bifunctional N,N′-dioxide catalysts have been developed for highly enantioselective cyanosilylation of α,α-dialkoxy ketones. This process, catalyzed by in-situ-prepared proline-derived N,N′-dioxide 2b, produced the corresponding cyanohydrin trimethylsilyl ethers in excellent yields (up to 99%) with high enantioselectivities (up to 93% ee). A reasonable mechanism was proposed according to the observation of the linear effect, 1H NMR spectra, isolated cyanohydrin, and the roles of the NH and N-oxide moieties of the catalyst.
