Stereoselective reductive radical cyclization of ketonitriles catalyzed by Cp2TiCl2 in the presence of chlorosilane and zinc

被引：32

作者：

Zhou, LH ^{[1
]}

Hirao, T ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2001年 / 57卷 / 32期

基金：

日本学术振兴会;

关键词：

titanium catalyst; one-electron reduction; diastereoselective cyclization; silylating reagent; co-reductant;

D O I：

10.1016/S0040-4020(01)00645-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reductive radical cyclization of ketonitriles was catalyzed by Cp2TiCl2 in the presence Of Me3SiCl, zinc powder and imidazole, giving the 2-amino-3-cyano-2-cyclopenten-1-ols in moderate to good yields with high trans selectivity (up to 94% trans). The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereoselectivity of the cyclized products was investigated in detail. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6927 / 6933

页数：7

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