Enantioselective cyanosilylation of aldehydes catalyzed by a novel N,N′-dioxide-Ti(OiPr)4 bifunctional catalyst

被引：24

作者：

Zeng, Baiqing ^{[1
]}

Zhou, Xin ^{[1
]}

Liu, Xiaohua ^{[1
]}

Feng, Xiaoming ^{[1
]}

机构：

[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China

来源：

TETRAHEDRON | 2007年 / 63卷 / 24期

基金：

中国国家自然科学基金;

关键词：

asymmetric catalysis; cyanosilylation; Lewis acid; Lewis base; bifunctional catalyst;

D O I：

10.1016/j.tet.2007.04.008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel bifunctional asymmetric catalyst containing N-oxide and titanium(IV) was developed and applied to the asymmetric cyanosilylation of aldehydes. Optically active trimethylsilyl cyanohydrin ethers were obtained up to 99% yield and 80% ee in the presence of 5 mol % catalyst loading at -78 degrees C. Based on the experimental results, the catalytic cycle was proposed as a pathway in which Lewis acid and Lewis base activated aldehyde and trimethylsilylcyanide (TMSCN), respectively. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：5129 / 5136

页数：8

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