Asymmetric conjugate addition of diethyl zinc to enones with chiral phosphine ligands

被引：52

作者：

Alexakis, A ^{[1
]}

Burton, J ^{[1
]}

Vastra, J ^{[1
]}

Mangeney, P ^{[1
]}

机构：

[1] Univ Paris 06, URA 473 CNRS, Lab Chim Organoelements, F-75252 Paris 05, France

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 24期

关键词：

D O I：

10.1016/S0957-4166(97)00523-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral bidentate aryl- and alkyl phosphines (0.5%) coordinated to copper(II) triflate (0.5%) are efficient catalysts for the asymmetric conjugate addition of diethyl zinc to cyclohexen-2-one, chalcone and benzalacetone. Among the chiral phosphines tested, (S)-Norphos, (S,S)-Chiraphos and (R)-Prophos gave the best enantiomeric excesses (44%, 44% and 36% respectively). (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：3987 / 3990

页数：4

共 21 条

[1] ENANTIOSELECTIVE CONJUGATE ADDITION OF GRIGNARD-REAGENTS TO ENONES CATALYZED BY CHIRAL CUPRATE COMPLEXES [J].

AHN, KH ;

KLASSEN, RB ;

LIPPARD, SJ .

ORGANOMETALLICS, 1990, 9 (12) :3178-3181

[2] CHIRAL PHOSPHORUS LIGANDS FOR THE ASYMMETRIC CONJUGATE ADDITION OF ORGANOCOPPER REAGENTS [J].

ALEXAKIS, A ;

FRUTOS, J ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2427-2430

[3]

ALEXAKIS A, 1997, TETRAHEDRON LETT, V38, P1019

[4]

ALEXAKIS A, 1994, ORGANOCOPPER REAGENT, P159

[5]

[Anonymous], 1995, ADV CAT PROCESS

[6]

BRIES AHM, 1996, ANGEW CHEM INT EDIT, V35, P2374

[7]

Brunner H., 1993, HDB ENANTIOSELECTIVE

[8] Diastereoselective synthesis of pyridyl substituted thiazolidin-4-ones. New ligands for the Cu(I) catalyzed asymmetric conjugate addition of diethylzinc to enones [J].

deVries, AHM ;

Hof, RP ;

Staal, D ;

Kellogg, RM ;

Feringa, BL .

TETRAHEDRON-ASYMMETRY, 1997, 8 (10) :1539-1543

[9] ASYMMETRIC CONJUGATE ADDITION OF ORGANOMAGNESIUM CUPRATES CONTROLLED BY A STOICHIOMETRIC AMOUNT OF CHIRAL PHOSPHINE [J].

KANAI, M ;

TOMIOKA, K .

TETRAHEDRON LETTERS, 1995, 36 (24) :4273-4274

[10] A NEW CLASS OF ORGANOCOPPER AND ORGANOCUPRATE COMPOUNDS DERIVED FROM COPPER(I) ARENETHIOLATES [J].

KNOTTER, DM ;

GROVE, DM ;

SMEETS, WJJ ;

SPEK, AL ;

VANKOTEN, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (09) :3400-3410

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