Enantioselective copper-catalyzed conjugate addition of dialkyl zinc to nitro-olefins

被引：94

作者：

Alexakis, A ^{[1
]}

Benhaim, C ^{[1
]}

机构：

[1] Univ Geneva, Dept Organ Chem, CH-1211 Geneva 2, Switzerland

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 17期

关键词：

D O I：

10.1021/ol0059596

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The copper-catalyzed asymmetric conjugate addition of dialkylzinc onto various nitro-olefins has been carried out with excellent results, An enantiomeric excess of up to 94% was obtained using 0.5% Cu(OTf)(2) and 1% of chiral trivalent phosphorus ligand.

引用

页码：2579 / 2581

页数：3

共 22 条

[1]

Alexakis A, 1999, SYNLETT, P1811

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

Alexakis, A ;

Vastra, J ;

Mangeney, P .

TETRAHEDRON LETTERS, 1997, 38 (44) :7745-7748

[3] Asymmetric conjugate addition of diethyl zinc to enones with tartrate chiral phosphite ligands [J].

Alexakis, A ;

Vastra, J ;

Burton, J ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3193-3196

[4] NEW CHIRAL LIGAND FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS TO ENONES [J].

ALEXAKIS, A ;

MUTTI, S ;

NORMANT, JF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6332-6334

[5] Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands [J].

Alexakis, A ;

Burton, J ;

Vastra, J ;

Mangeney, P .

TETRAHEDRON-ASYMMETRY, 1997, 8 (24) :3987-3990

[6]

ALEXAKIS A, UNPUB

[7] HETEROSUBSTITUTED NITROALKENES IN SYNTHESIS [J].

BARRETT, AGM .

CHEMICAL SOCIETY REVIEWS, 1991, 20 (01) :95-127

[8]

Bernard D., 1974, PHOSPHORUS, V3, P187

[9] First diastereoselective asymmetric carbometallation of chiral vinyl metals. [J].

Brasseur, D ;

Rezaei, H ;

Fuxa, A ;

Alexakis, A ;

Mangeney, P ;

Marek, I ;

Normant, JF .

TETRAHEDRON LETTERS, 1998, 39 (27) :4821-4824

[10] Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents [J].

Feringa, BL ;

Pineschi, M ;

Arnold, LA ;

Imbos, R ;

de Vries, AHM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2620-2623

← 1 2 3 →