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

来源：

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL | 2003年 / 191卷 / 01期

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.

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页码：23 / 27

页数：5

相关论文

共 19 条

[1] Novel chiral diimines and diamines derived from sugars in copper-catalysed asymmetric cyclopropanation [J].

Borriello, C ;

Cucciolito, ME ;

Panunzi, A ;

Ruffo, F .

TETRAHEDRON-ASYMMETRY, 2001, 12 (17) :2467-2471

[2] Asymmetric cyclopropanation catalyzed by C2-symmetric bi(oxazolines) [J].

Boulch, R ;

Scheurer, A ;

Mosset, P ;

Saalfrank, RW .

TETRAHEDRON LETTERS, 2000, 41 (07) :1023-1026

[3] Polymer-supported bis(oxazoline)-copper complexes as catalysts in cyclopropanation reactions [J].

Burguete, MI ;

Fraile, JM ;

García, JI ;

García-Verdugo, E ;

Luis, SV ;

Mayoral, JA .

ORGANIC LETTERS, 2000, 2 (24) :3905-3908

[4] Mesopore immobilised copper bis(oxazoline) complexes for enantioselective catalysis [J].

Clarke, RJ ;

Shannon, IJ .

CHEMICAL COMMUNICATIONS, 2001, (19) :1936-1937

[5] Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis [J].

Fache, F ;

Schulz, E ;

Tommasino, ML ;

Lemaire, M .

CHEMICAL REVIEWS, 2000, 100 (06) :2159-2231

[6]

FUKUDA T, 1995, SYNLETT, P825

[7] Novel macrocyclic heterodinuclear catalase-like model complex CuMnL and CuZnL (L = BDBPH): synthesis, stability and catalytic properties [J].

Gao, J ;

Martell, AE ;

Motekaitis, RJ .

INORGANICA CHIMICA ACTA, 2001, 325 (1-2) :164-170

[8] C2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis [J].

Ghosh, AK ;

Packiarajan, M ;

Cappiello, J .

TETRAHEDRON-ASYMMETRY, 1998, 9 (01) :1-45

[9] Conformational analysis of cationic (R,S)- and (R,R)-(salen)manganese complexes possessing axial chirality as a chiral element based on X-ray crystallography:: An explanation of the effect of apical ligand on enantioselection by (salen)manganese catalyst [J].

Hashihayata, T ;

Punniyamurthy, T ;

Irie, R ;

Katsuki, T ;

Akita, M ;

Moro-oka, Y .

TETRAHEDRON, 1999, 55 (51) :14599-14610

[10] Highly enantioselective cyclopropanation of styrenes with diazoacetates catalyzed by optically active β-ketoiminato cobalt(II) complexes [J].

Ikeno, T ;

Sato, M ;

Yamada, T .

CHEMISTRY LETTERS, 1999, (12) :1345-1346