Palladium-catalyzed enantioselective synthesis of cyclohexene derivatives via kinetic resolution

被引：25

作者：

Nishimata, T

Yamaguchi, K

Mori, M ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Kita Ku, Sapporo, Hokkaido 0600812, Japan

[2] Chiba Univ, Ctr Chem Anal, Inage Ku, Chiba 2630022, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 31期

关键词：

asymmetric synthesis; (pi-ally)palladium complex; kinetic resolution; Pd(2)dba center dot CHCl3; (S)-BINAPO;

D O I：

10.1016/S0040-4039(99)01079-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of (+/-)-methyl 2-arylcyclohexenyl carbonate with tosyl amide in the presence of a catalytic amount of Pd(2)dba-CHCl3 and (S)-BINAPO produced 2-arylcyclohexenyl tosyl amide with a high ee along with the starting material with a high ee. The reaction involved two processes, and (+)- and (-)-methy] 2-arylcyclohexenyl carbonate gave the same (pi-allyl)palladium complex with a chiral ligand, which gave 2-arylcyclohexenyl tosyl amide with a high ee by enantioselective substitution. The intermediary (pi-allyl)palladium complex was synthesized, and the results of X-ray crystallography are shown. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5713 / 5716

页数：4

共 10 条

[1] Pd-catalyzed asymmetric synthesis of allylic tert-butyl sulfones and sulfides:: Kinetic resolution of the allylic substrate by a chiral Pd-complex [J].