Concave reagents .22. Cyclopropanation of alkenes with ethyl diazoacetate: Copper(I) complexes of concave 1,10-phenanthrolines as diastereoselective catalysts

被引:27
作者
Hagen, M [1 ]
Luning, U [1 ]
机构
[1] CHRISTIAN ALBRECHTS UNIV KIEL,INST ORGAN CHEM,D-24098 KIEL,GERMANY
来源
CHEMISCHE BERICHTE-RECUEIL | 1997年 / 130卷 / 02期
关键词
diastereoselective cyclopropanation; copper compounds; homogeneous catalysis; molecular recognition; bimacrocycles; alkenes; macrocyclic ligands; heterocycles;
D O I
10.1002/cber.19971300215
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Concave 1,10-phenanthrolines 1a-c have been used as ligands in the copper(I)-catalyzed cyclopropanation of alkenes 2 with ethyl diazoacetate. The complexes proved to be efficient cyclopropanation catalysts and exhibited an enhanced diastereoselectivity, particularly in the reactions of cyclic alkenes 2b-d. the preferred formation of exo-cyclopropanes 3b-d can be explained by the concave shape of these catalysts.
引用
收藏
页码:231 / 234
页数:4
相关论文
共 28 条
[1]   TRANSMISSION OF ELECTRONIC EFFECTS THROUGH CYCLOPROPANE .2. COMPARATIVE MODULATION OF H-1 CHEMICAL-SHIFTS BY ARYLOXY AND ARYL SUBSTITUENTS IN 2-(DONOR)-1-(ACCEPTOR)CYCLOPROPANES [J].
ALONSO, ME ;
PEKERAR, SV .
MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (06) :587-593
[2]   A new class of bis-oxazoline ligands for the Cu-catalysed asymmetric cyclopropanation of olefins [J].
Bedekar, AV ;
Andersson, PG .
TETRAHEDRON LETTERS, 1996, 37 (23) :4073-4076
[3]   A TRANSITION-STATE MODEL FOR THE RHODIUM PORPHYRIN-CATALYZED CYCLOPROPANATION OF ALKENES BY DIAZO ESTERS [J].
BROWN, KC ;
KODADEK, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8336-8338
[4]   CYCLOPROPANATION USING RHODIUM(III)PORPHYRINS - LARGE CIS VS TRANS SELECTIVITY [J].
CALLOT, HJ ;
PIECHOCKI, C .
TETRAHEDRON LETTERS, 1980, 21 (36) :3489-3492
[5]   Osmium-catalysed cyclopropanation of olefins [J].
Demonceau, A ;
Lemoine, CA ;
Noels, AF .
TETRAHEDRON LETTERS, 1996, 37 (07) :1025-1026
[6]   OLEFIN CYCLOPROPANATION REACTIONS CATALYZED BY NOVEL RUTHENACARBORANE CLUSTERS [J].
DEMONCEAU, A ;
SAIVE, E ;
DEFROIDMONT, Y ;
NOELS, AF ;
HUBERT, AJ ;
CHIZHEVSKY, IT ;
LOBANOVA, IA ;
BREGADZE, VI .
TETRAHEDRON LETTERS, 1992, 33 (15) :2009-2012
[7]   CYCLOPROPANATION CATALYZED BY RUCL2(PPH(3))(3) AND OSCL2(PPH(3))(3) [J].
DEMONCEAU, A ;
LEMOINE, CA ;
NOELS, AF ;
CHIZHEVSKY, IT ;
SOROKIN, PV .
TETRAHEDRON LETTERS, 1995, 36 (46) :8419-8422
[8]   EFFECTS OF SECONDARY INTERACTIONS ON THE STEREOCHEMICAL OUTCOME OF RHODIUM(II) CARBOXYLATE CATALYZED CYCLOPROPANATION OF OLEFINS [J].
DEMONCEAU, A ;
NOELS, AF ;
HUBERT, AJ .
TETRAHEDRON, 1990, 46 (11) :3889-3896
[9]  
DOYLE MP, 1991, RECL TRAV CHIM PAY B, V110, P305
[10]   EXCEPTIONALLY HIGH TRANS (ANTI) STEREOSELECTIVITY IN CATALYTIC CYCLOPROPANATION REACTIONS [J].
DOYLE, MP ;
BAGHERI, V ;
WANDLESS, TJ ;
HARN, NK ;
BRINKER, DA ;
EAGLE, CT ;
LOH, KL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1906-1912