Acceleration of the conjugate addition of diethyl zinc to enones by either Cu(OTf)(2) or trivalent phosphorus ligands

被引：80

作者：

Alexakis, A

Vastra, J

Mangeney, P

机构：

[1] Lab. de Chim. des Organo-Elements, Associé au CNRS URA 473, Univ. Pierre et Marie Curie, 75252 Paris Cedex 05, 4, Place Jussieu

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 44期

关键词：

D O I：

10.1016/S0040-4039(97)10068-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The conjugate addition of diethyl zinc to enones under copper catalysis occurs well with copper (II) triflate. Other copper salts need a phosphine or phosphite ligand to be efficient. The best combination is copper (II) triflate and triethyl phosphite. A very small amount of copper (II) triflate (0.5%) and triehtyl phosphite (1%) are enough for high yields. (C) 1997 Elsevier Science Ltd.

引用

页码：7745 / 7748

页数：4

共 22 条

[1] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS
ALEXAKIS, A
FRUTOS, J
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2427 - 2430
[2] OPTICALLY-ACTIVE BIPYRIDINES IN NICKEL CATALYZED ENANTIOSELECTIVE CONJUGATE ADDITION TO ENONES
BOLM, C
EWALD, M
[J]. TETRAHEDRON LETTERS, 1990, 31 (35) : 5011 - 5012
[3] Enantioselective conjugate addition of dialkylzinc reagents to cyclic and acyclic enones catalyzed by chiral copper complexes of new phosphorus amidites
deVries, AHM
Meetsma, A
Feringa, BL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (20): : 2374 - 2376
[4] EFFICIENT SYNTHESES OF (+/-)-BETA-CUPARENONE - CONJUGATE ADDITION OF ORGANOZINC REAGENTS
GREENE, AE
LANSARD, JP
LUCHE, JL
PETRIER, C
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (05) : 931 - 932
[5] CATALYTIC ENANTIOSELECTIVE CONJUGATE ADDITION OF DIETHYLZINC USING NI(II) DAIB COMPLEXES
JANSEN, JFGA
FERINGA, BL
[J]. TETRAHEDRON-ASYMMETRY, 1992, 3 (05) : 581 - 582
[6] ZINC(II) CATALYZED CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ALPHA-BETA-UNSATURATED KETONES
JANSEN, JFGA
FERINGA, BL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (11) : 741 - 742
[7] Conjugate addition of diorganozincs to alpha,beta-unsaturated ketones catalyzed by a copper(I)-sulfonamide combined system
Kitamura, M
Miki, T
Nakano, K
Noyori, R
[J]. TETRAHEDRON LETTERS, 1996, 37 (29) : 5141 - 5144
[8] PREPARATION AND REACTIONS OF POLYFUNCTIONAL ORGANOZINC REAGENTS IN ORGANIC-SYNTHESIS
KNOCHEL, P
SINGER, RD
[J]. CHEMICAL REVIEWS, 1993, 93 (06) : 2117 - 2188
[9] Kozlowski J. A, 1991, COMPREHENSIVE ORGANI, V4, P169
[10] Krause N, 1997, ANGEW CHEM INT EDIT, V36, P187

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