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
收藏
页码：6927 / 6933
页数：7
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