Effect of rhodium carbenoid structure on cyclopropanation chemoselectivity

被引：117

作者：

Davies, HML ^{[1
]}

Panaro, SA ^{[1
]}

机构：

[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 28期

关键词：

cyclopropanation; carbenes and carbenoids; diazo compounds; rhodium catalysis;

D O I：

10.1016/S0040-4020(00)00202-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium-stabilized carbenoids derived from aryldiazoacetates and vinyldiazoacetates undergo highly chemoselective intermolecular cyclopropanations, and this selectivity has been quantified by a Hammett study. These donor/acceptor substituted carbenoids are much more chemoselective than the traditional carbenoids derived from alkyl diazoacetates. (C) 2000 Published by Elsevier Science Ltd.

引用

页码：4871 / 4880

页数：10

共 59 条

[41] New aspects of catalytic asymmetric cyclopropanation
Doyle, MP
Protopopova, MN
[J]. TETRAHEDRON, 1998, 54 (28) : 7919 - 7946
[42] EXCEPTIONALLY HIGH TRANS (ANTI) STEREOSELECTIVITY IN CATALYTIC CYCLOPROPANATION REACTIONS
DOYLE, MP
BAGHERI, V
WANDLESS, TJ
HARN, NK
BRINKER, DA
EAGLE, CT
LOH, KL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) : 1906 - 1912
[43] BIS(OXAZOLINES) AS CHIRAL LIGANDS IN METAL-CATALYZED ASYMMETRIC REACTIONS - CATALYTIC, ASYMMETRIC CYCLOPROPANATION OF OLEFINS
EVANS, DA
WOERPEL, KA
HINMAN, MM
FAUL, MM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) : 726 - 728
[44] SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .1. SYNTHESIS OF CHIRAL SEMICORRIN LIGANDS AND GENERAL CONCEPTS
FRITSCHI, H
LEUTENEGGER, U
SIEGMANN, K
PFALTZ, A
KELLER, W
KRATKY, C
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (06) : 1541 - 1552
[45] SEMICORRIN METAL-COMPLEXES AS ENANTIOSELECTIVE CATALYSTS .2. ENANTIOSELECTIVE CYCLOPROPANE FORMATION FROM OLEFINS WITH DIAZO-COMPOUNDS CATALYZED BY CHIRAL (SEMICORRINATO)COPPER COMPLEXES
FRITSCHI, H
LEUTENEGGER, U
PFALTZ, A
[J]. HELVETICA CHIMICA ACTA, 1988, 71 (06) : 1553 - 1565
[46] Ishitani H, 1997, SYNLETT, P781
[47] ASYMMETRIC CATALYTIC CYCLOPROPANATION OF OLEFINS - BIS-OXAZOLINE COPPER-COMPLEXES
LOWENTHAL, RE
ABIKO, A
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1990, 31 (42) : 6005 - 6008
[48] ASYMMETRIC COPPER-CATALYZED CYCLOPROPANATION OF TRISUBSTITUTED AND UNSYMMETRICAL CIS-1,2-DISUBSTITUTED OLEFINS - MODIFIED BIS-OXAZOLINE LIGANDS
LOWENTHAL, RE
MASAMUNE, S
[J]. TETRAHEDRON LETTERS, 1991, 32 (50) : 7373 - 7376
[49] MAAS G, 1987, TOP CURR CHEM, V137, P75
[50] SHAPE-SELECTIVE AND ASYMMETRIC CYCLOPROPANATION OF ALKENES CATALYZED BY RHODIUM PORPHYRINS
MAXWELL, JL
OMALLEY, S
BROWN, KC
KODADEK, T
[J]. ORGANOMETALLICS, 1992, 11 (02) : 645 - 652

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