CATALYTIC ASYMMETRIC REDUCTIVE AMINATION OF KETONES VIA HIGHLY ENANTIOSELECTIVE HYDROGENATION OF THE C=N DOUBLE-BOND

被引：144

作者：

BURK, MJ

MARTINEZ, JP

FEASTER, JE

COSFORD, N

机构：

[1] DUPONT CO INC,CENT RES & DEV,EXPTL STN,WILMINGTON,DE 19880

[2] DUPONT MERCK PHARMACEUT CO,WILMINGTON,DE 19880

来源：

TETRAHEDRON | 1994年 / 50卷 / 15期

关键词：

D O I：

10.1016/S0040-4020(01)89375-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a convenient, chemoselective asymmetric reductive amination procedure for the conversion of ketones to chiral hydrazines and amines. The key step in the three-step process is enantioselective DuPHOS-Rh-catalyzed hydrogenation of the C=N double bond of N-acylhydrazones. Detailed optimization studies revealed the effect of solvent, temperature, and the N-acyl group on the enantioselectivity and catalytic efficiency of the reaction. The reduction products, N-acylhydrazines, were converted to hydrazines or amines through hydrolysis or treatment with samarium(II) iodide, respectively.

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页码：4399 / 4428

页数：30

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