Design and synthesis of new bidentate alkoxy-NHC ligands for enantio selective copper-catalyzed conjugate addition

被引：138

作者：

Clavier, H ^{[1
]}

Coutable, L ^{[1
]}

Toupet, L ^{[1
]}

Guillemin, JC ^{[1
]}

Mauduit, M ^{[1
]}

机构：

[1] Univ Rennes 1, Grp Mat Condensees & Mat, CNRS, UMR 6626, F-35700 Rennes, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2005年 / 690卷 / 23期

关键词：

chiral N-heterocyclic carbene; alkoxy-imidazolinium salts; asymmetric catalysis;

D O I：

10.1016/j.jorganchem.2005.04.027

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new family of chiral alkoxy-N-heterocyclic carbene (NHC) ligands has been designed for the enantioselective copper-catalyzed conjugate addition of dialkylzincs to enones. These new bidentate NHC ligands were synthesized in high overall yields using a five-step procedure starting from commercially available beta-aminoalcohols. Influence of the temperature, base, solvent and copper source were studied in order to optimize the stereoselectivity of the addition. High reactivity and excellent enantioselectivity were obtained at ambient temperature with a range of cyclic enones and dialkylzinc. Addition to acyclic enones has also been studied. (c) 2005 Elsevier B.V. All rights reserved.

引用

页码：5237 / 5254

页数：18

共 38 条

[1] Asymmetric synthesis with N-heterocyclic carbenes.: Application to the copper-catalyzed conjugate addition [J].

Alexakis, A ;

Winn, CL ;

Guillen, F ;

Pytkowicz, J ;

Roland, S ;

Mangeney, P .

ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (03) :345-348

[2] SIR97:: a new tool for crystal structure determination and refinement [J].

Altomare, A ;

Burla, MC ;

Camalli, M ;

Cascarano, GL ;

Giacovazzo, C ;

Guagliardi, A ;

Moliterni, AGG ;

Polidori, G ;

Spagna, R .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119

[3] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

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

ARDUENGO, AJ ;

DIAS, HVR ;

CALABRESE, JC ;

DAVIDSON, F .

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

[5] Asymmetric lithium(I) and copper(II) alkoxy-N-heterocyclic carbene complexes;: crystallographic characterisation and Lewis acid catalysis [J].

Arnold, PL ;

Rodden, M ;

Davis, KM ;

Scarisbrick, AC ;

Blake, AJ ;

Wilson, C .

CHEMICAL COMMUNICATIONS, 2004, (14) :1612-1613

[6] Chelating alkoxy-N-heterocyclic carbene complexes of silver and copper [J].

Arnold, PL ;

Scarisbrick, AC ;

Blake, AJ ;

Wilson, C .

CHEMICAL COMMUNICATIONS, 2001, (22) :2340-2341

[7] Synthesis and application of complexes of a novel chiral diphenylphosphino-functionalized N-heterocyclic carbene [J].

Bappert, E ;

Helmchen, G .

SYNLETT, 2004, (10) :1789-1793

[8] Synthesis of new chiral N-heterocyclic carbene-imine ligands and their application to an asymmetric allylic alkylation reaction [J].

Bonnet, LG ;

Douthwaite, RE ;

Kariuki, BM .

ORGANOMETALLICS, 2003, 22 (21) :4187-4189

[9] Stable carbenes [J].

Bourissou, D ;

Guerret, O ;

Gabbaï, FP ;

Bertrand, G .

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

[10] Chiral N-heterocyclic carbenes as stereodirecting ligands in asymmetric catalysis [J].

César, V ;

Bellemin-Laponnaz, S ;

Gade, LH .

CHEMICAL SOCIETY REVIEWS, 2004, 33 (09) :619-636

← 1 2 3 4 →