Complete retention of Z geometry in allylic substitution catalyzed by an iridium complex

被引：61

作者：

Takeuchi, R

Shiga, N

机构：

[1] Yokohama City Univ, Fac Sci, Dept Environm Sci, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

[2] Yokohama City Univ, Grad Sch Integrated Sci, Kanazawa Ku, Yokohama, Kanagawa 2360027, Japan

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 02期

关键词：

D O I：

10.1021/ol990033n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Z geometry of methyl (Z)-3-monosubstituted-2-alkenyl carbonate was completely retained in iridium complex-catalyzed allylic amination. The reaction of methyl (Z)-2-nonenyl carbonate with piperidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) at 50 degrees C for 2 h gave a 98:2 mixture of (Z)-1-(2-nonenyl)piperidine and 1-(1-n-hexyl-2-propenyl)piperidine in 86% yield, No E isomer was obtained. Various (Z) allylic amines were obtained in 91-100% selectivity by allylic amination of methyl (Z) 3-monosubstituted-2-alkenyl carbonate.

引用

页码：265 / 267

页数：3

共 20 条

[1] AMINATION OF PI-ALLYLPALLADIUM CHLORIDE COMPLEXES - A MECHANISTIC STUDY [J].