Asymmetric cyanosilylation of ketones catalyzed by bifunctional chiral N-oxide titanium complex catalysts

被引：85

作者：

Shen, YC ^{[1
]}

Feng, XM

Li, Y

Zhang, GL

Jiang, YZ

机构：

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

[2] Chinese Acad Sci, Chengdu Inst Organ Chem, Chengdu 610064, Peoples R China

[3] Chinese Acad Sci, Chengdu Inst Biol, Chengdu 610064, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 01期

关键词：

asymmetric catalysis; asymmetric synthesis; enantioselectivity; ketones; N; O ligands;

D O I：

10.1002/ejoc.200300415

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new bifunctional catalytic system based on chiral N-oxide titanium complexes has been used for the asymmetric cyano-silylation of ketones. Screening of a variety of chiral N-oxide metal complexes resulted in (1R,2S)-1-(2'-pyridylmethyl)-2-(diphenylhydroxymethyl)pyrrolidine N-oxide titanium complex, which gave O-TMS cyanohydrins in good yields with enantiomeric excesses of up to 69%. A catalytic cycle based on experimental phenomena and studies was proposed to explain the origin of the asymmetric induction. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).

引用

页码：129 / 137

页数：9

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