Enantioselective cyanosilylation of ketones catalyzed by a nitrogen-containing bifunctional catalyst

被引：83
作者：
Xiong, Y
Huang, X
Gou, SH
Huang, JL
Wen, YH
Feng, XM [1 ]
机构：
[1] Sichuan Univ, Minist Educ, Coll Chem, Key Lab Green Chem & Technol, Chengdu 610064, Peoples R China
[2] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 4-5期
关键词：
amides; bifunctional catalysts; cyanosilylation; hypervalent silicon; ketones; titanium;
D O I：
10.1002/adsc.200505418
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient and optically active, bifunctional tetraazaligand (2S)-N-{(1R,2R)-2-[(S)-pyrrolidine2-carboxamido]-1,2-diphenylethyl}pyrrolidine-2-carboxamide has been developed for the addition of trimethylsilyl cyanide (TMSCN) to ketones. The bifunctional catalyst system based on a monometallic titanium complex was found to be a highly enantioselective catalyst to provide O-TMS cyanohydrins with up to 94% ee. A possible transition state has been proposed to explain the origin of the activation and asymmetric inductivity.
引用
收藏
页码：538 / 544
页数：7
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