COPPER(II) IN ORGANIC-SYNTHESIS .11. EVALUATION DF THE LIGAND ARCHITECTURE ON THE EFFICIENCY OF A COPPER(II) CATALYST FOR ENANTIOSELECTIVE MICHAEL REACTIONS

被引:52
作者
DESIMONI, G
DUSI, G
FAITA, G
QUADRELLI, P
RIGHETTI, P
机构
[1] Dipartimento di Chimica Organica dell'Università, I-27100 Pavia
关键词
D O I
10.1016/0040-4020(95)00130-Z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Several bis-copper (II) complexes with chiral ligands derived from 2-substituted 2-(salicylideneamino) ethanols have been tested as catalysts of enantioselective Michael reactions. The degree of enantioselection is strongly affected by the architecture of the ligand. The best result (75% e.e.) was obtained for a ligand having a substituent potentially suitable to induce the formation of a bis-tetradentate copper (II) complex with a square pyramidal coordination.
引用
收藏
页码:4131 / 4144
页数:14
相关论文
共 24 条
[1]  
AOKI S, 1992, HETEROCYCLES, V33, P493
[3]   CRYSTAL AND MOLECULAR-STRUCTURES AND MAGNETIC-PROPERTIES OF TETRAMERIC COPPER(II) COMPLEXES WITH 3-HYDROXY-5-HYDROXYMETHYL-4-(4'-HYDROXY-4'-PHENYL-2'-AZABUT-1'-EN-1'-YL)-2-METHYLPYRIDINE (H2L3),([CU4L3]-L-4).9CH3OH AND 3-HYDROXY-5-HYDROXYMETHYL-4-(4'-HYDROXY-3'-METHYL-4'-PHENYL-2'AZABUT-1'-EN-1'-YL)-2-METHYLPYRIDINE (H2L1), ([CU4L1]-L-4).8CH3CH2OH - 2 COMPLEXES WITH FERROMAGNETIC GROUND-STATESO [J].
ASTHEIMER, H ;
NEPVEU, F ;
WALZ, L ;
HAASE, W .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1985, (02) :315-320
[4]   ASYMMETRIC-SYNTHESIS OF THREONINE AND PARTIAL RESOLUTION AND RETRORACEMIZATION OF ALPHA-AMINO-ACIDS VIA COPPER(II) COMPLEXES OF THEIR SCHIFF-BASES WITH (S)-2-N-(N'-BENZYLPROLYL)AMINOBENZALDEHYDE AND (S)-2-N-(N'-BENZYLPROLYL)AMINOACETOPHENONE - CRYSTAL AND MOLECULAR-STRUCTURE OF A COPPER(II) COMPLEX OF GLYCINE SCHIFF-BASE WITH (S)-2-N-(N'-BENZYLPROLYL)AMINOACETOPHENONE(S [J].
BELOKON, YN ;
ZELTZER, IE ;
BAKHMUTOV, VI ;
SAPOROVSKAYA, MB ;
RYZHOV, MG ;
YANOVSKY, AI ;
STRUCHKOV, YT ;
BELIKOV, VM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (07) :2010-2017
[5]  
BONADIES F, 1993, TETRAHEDRON LETT, V3, P7649
[6]  
BOTTEGHI C, 1991, J MOL CATAL, V6, P7
[7]   HERSTELLUNG VON ALPHA-AMINOSAUREESTERN DURCH ALKOHOLYSE DER METHYLESTER [J].
BRENNER, M ;
HUBER, W .
HELVETICA CHIMICA ACTA, 1953, 36 (05) :1109-1115
[8]   ASYMMETRIC CATALYSIS .18. ENANTIOSELECTIVE MICHAEL ADDITIONS WITH OPTICALLY-ACTIVE COII/DIAMINE CATALYSTS [J].
BRUNNER, H ;
HAMMER, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (04) :312-313
[9]   ASYMMETRICAL CATALYSTS .21. ENANTIOSELECTIVE CYCLOPROPANATION OF 1,1-DIPHENYLETHYLENE AND DIAZOACETIC ACID ESTER WITH COPPER-CATALYSTS [J].
BRUNNER, H ;
MIEHLING, W .
MONATSHEFTE FUR CHEMIE, 1984, 115 (10) :1237-1254
[10]   EXCHANGE INTERACTION IN MULTINUCLEAR TRANSITION-METAL COMPLEXES .13. EXCHANGE COUPLING IN CU2L2CL2.2CH3OH (LH=8-(SALICYLIDENEAMINO)QUINOLINE), A NEW COMPOUND WITH A TEMPERATURE-DEPENDENT STRUCTURE [J].
CHIARI, B ;
PIOVESANA, O ;
TARANTELLI, T ;
ZANAZZI, PF .
INORGANIC CHEMISTRY, 1989, 28 (11) :2141-2145