Cp2VCl2-catalyzed meso-selective pinacol coupling reaction of aldimines in the presence of chlorosilane and zinc metal

被引：78

作者：

Hatano, B ^{[1
]}

Ogawa, A ^{[1
]}

Hirao, T ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 25期

关键词：

D O I：

10.1021/jo981396o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic reductive coupling of aldimines was achieved by using a catalyst Cp(2)VCl(2)/PhMe(2)SiCl/Zn system. The influence of the catalyst, chlorosilane, co-reductant, solvent, and temperature on both the yield and diastereoselectivity of the coupling products was investigated in detail. As a result, the present Cp(2)VCl(2)-catalyzed reductive coupling of aldimines in the presence of PhMe(2)SiCl and zinc metal provided the corresponding 1,2-diamines in good yield with high meso selectivity (up to 92% meso), while the reductive coupling of aldehydes, ketones, and aldimines by the hitherto known catalytic methods leads to the preferential formation of dl isomers of the coupling products.

引用

页码：9421 / 9424

页数：4

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