Enantioselective conjugate addition of diethylzinc using catalytic silver(I) diaminocarbenes and Cu(OTf)2

被引：93

作者：

Pytkowicz, J ^{[1
]}

Roland, S ^{[1
]}

Mangeney, P ^{[1
]}

机构：

[1] Univ Paris 06, UMR 7611, Lab Chim Organoelements, F-75252 Paris 05, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 15期

关键词：

D O I：

10.1016/S0957-4166(01)00325-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Chiral silver(I) diaminocarbenes act as efficient carbene transfer agents to copper salts. The catalytic species, active in the conjugate addition of diethylzinc to cyclohexenone, is prepared easily at room temperature in various solvents by simply mixing the silver carbene and Cu(OTf)(2). This method avoids the use of strong bases and polar solvents to generate the carbene. The chiral diaminocarbene-copper catalyst, formed in situ, shows a strong accelerating effect and gives enantiomeric excesses up to 23%. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：2087 / 2089

页数：3

共 23 条

[1] AN EASY AND FAST WAY TO DETERMINE THE ENANTIOMERIC PURITY OF SUBSTITUTED CYCLANONES [J].

ALEXAKIS, A ;

FRUTOS, JC ;

MANGENEY, P .

TETRAHEDRON-ASYMMETRY, 1993, 4 (12) :2431-2434

[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] HOMOLEPTIC CARBENE SILVER(I) AND CARBENE COPPER(I) COMPLEXES [J].

ARDUENGO, AJ ;

DIAS, HVR ;

CALABRESE, JC ;

DAVIDSON, F .

ORGANOMETALLICS, 1993, 12 (09) :3405-3409

[4] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

CHEMICAL REVIEWS, 2000, 100 (01) :39-91

[5]

Caló V, 2000, EUR J ORG CHEM, V2000, P869

[6] Heck reaction in ionic liquids catalyzed by a Pd-benzothiazole carbene complex [J].

Calò, V ;

Nacci, A ;

Lopez, L ;

Mannarini, N .

TETRAHEDRON LETTERS, 2000, 41 (46) :8973-8976

[7] First chelated chiral N-Heterocyclic bis-carbene complexes [J].

Clyne, DS ;

Jin, J ;

Genest, E ;

Gallucci, JC ;

RajanBabu, TV .

ORGANIC LETTERS, 2000, 2 (08) :1125-1128

[8] Strong ligand accelerated catalysis by an Arduengo-type carbene in copper-catalysed conjugate addition [J].

Fraser, PK ;

Woodward, S .

TETRAHEDRON LETTERS, 2001, 42 (14) :2747-2749

[9] 1,2,4-triazole-3,5-diylidene: A building block for organometallic polymer synthesis [J].

Guerret, O ;

Sole, S ;

Gornitzka, H ;

Teichert, M ;

Trinquier, G ;

Bertrand, G .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (28) :6668-6669

[10] N-heterocyclic carbenes [J].

Herrmann, WA ;

Kocher, C .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (20) :2162-2187

← 1 2 3 →