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
收藏
页码：5129 / 5136
页数：8
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