Asymmetric cyclopropanation catalyzed by C2-symmetric bis-(ephedrine)-Cu(II) complexes

被引:6
作者
Gao, JA [1 ]
Zhong, SH
机构
[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA
[2] Tianjin Univ, Coll Chem Engn & Technol, Tianjin 300072, Peoples R China
关键词
cyclopropanation; chiral ligand; asymmetric; ephedrine;
D O I
10.1016/S1381-1169(02)00326-6
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The asymmetric cyclopropanation of styrene with alkyl diazoacetate was performed with a series of Cu(II) complexes of novel chiral ligands, which were derived from substitution of 1,3-dibromopropane, 1,2-dibromoethane, alpha,alpha'-dibromo-m-xylene and 2,6-bis(bromomethyl)pyridine with 1R, 2S-(-)-ephedrine. These prepared catalysts shown to be highly active in the enantioselective cyclopropanation with ee higher than 89% under the optimal conditions. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:23 / 27
页数:5
相关论文
共 19 条
[11]   Asymmetric cyclopropanation catalyzed by copper-Schiff's base complexes [J].
Li, ZN ;
Zheng, Z ;
Wan, BS ;
Chen, HL .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 165 (1-2) :67-71
[12]   Synthesis of imine-amine type of chiral ligands and their application in the asymmetric cyclopropanation of olefins with diazoacetates [J].
Ma, JA ;
Wang, LX ;
Zhang, W ;
Zhou, QL .
TETRAHEDRON-ASYMMETRY, 2001, 12 (20) :2801-2804
[13]  
MIIMI T, 2000, TETRAHEDRON LETT, V41, P3647
[14]   C2-SYMMETRICAL 4,4',5,5'-TETRAHYDROBI(OXAZOLES) AND 4,4',5,5'-TETRAHYDRO-2,2'-METHYLENEBIS[OXAZOLES] AS CHIRAL LIGANDS FOR ENANTIOSELECTIVE CATALYSIS [J].
MULLER, D ;
UMBRICHT, G ;
WEBER, B ;
PFALTZ, A .
HELVETICA CHIMICA ACTA, 1991, 74 (01) :232-240
[15]  
PFALTZ A, 1990, CHIMIA, V44, P202
[16]   Design of chiral ligands for asymmetric catalysis: From C-2-symmetric semicorrins and bisoxazolines to non-symmetric phosphinooxazolines [J].
Pfaltz, A .
ACTA CHEMICA SCANDINAVICA, 1996, 50 (03) :189-194
[17]   CHIRAL SEMICORRINS AND RELATED NITROGEN-HETEROCYCLES AS LIGANDS IN ASYMMETRIC CATALYSIS [J].
PFALTZ, A .
ACCOUNTS OF CHEMICAL RESEARCH, 1993, 26 (06) :339-345
[18]  
Uchida T, 1999, SYNLETT, P1163
[19]   Optically active aldiminato cobalt(II) complexes as efficient catalysts for enantioselective cyclopropanation of styrenes with diazoacetates [J].
Yamada, T ;
Ikeno, T ;
Sekino, H ;
Sato, M .
CHEMISTRY LETTERS, 1999, (08) :719-720