Novel chiral copper complexes of NP-ferrocenyl ligands with central and planar chirality as efficient catalyst for asymmetric addition of diethylzinc to immes

被引：33

作者：

Wang, MC ^{[1
]}

Liu, LT ^{[1
]}

Hua, YZ ^{[1
]}

Zhang, JS ^{[1
]}

Shi, YY ^{[1
]}

Wang, DK ^{[1
]}

机构：

[1] Zhengzhou Univ, Dept Chem, Zhengzhou 450052, Peoples R China

来源：

TETRAHEDRON-ASYMMETRY | 2005年 / 16卷 / 15期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1016/j.tetasy.2005.06.005

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new type of chiral copper complexes of N,P-ferrocenyl ligands with central and planar chirality as efficient catalyst was applied to the enantioselective addition of diethylzinc to N-diphenylphosphinoylimines. The (R)- and (s)-enantiomers of the addition reaction were obtained for this transformation. In the presence of 6 mol % of bidentate ligand 1 and 12 mol % of Cu(OTf)(2), the asymmetric addition process affords N-diphenylphosphinoylamides in up to 97% ee and 95% yields. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：2531 / 2534

页数：4

共 64 条

[1] 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

[2] 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

[3] Preparation and use of aziridino alcohols as promoters for the enantioselective addition of dialkylzinc reagents to N-(diphenylphosphinoyl) imines [J].

Andersson, PG ;

Guijarro, D ;

Tanner, D .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7364-7375

[4] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity [J].

Bloch, R .

CHEMICAL REVIEWS, 1998, 98 (04) :1407-1438

[5] Asymmetric, catalytic synthesis of α-chiral amines using a novel bis(phosphine) monoxide chiral ligand [J].

Boezio, AA ;

Pytkowicz, J ;

Côté, A ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (47) :14260-14261

[6] Catalytic enantioselective addition of dialkylzinc to N-diphenylphosphinoylimines.: A practical synthesis of α-chiral amines [J].

Boezio, AA ;

Charette, AB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (07) :1692-1693

[7]

Brandt P, 1999, CHEM-EUR J, V5, P1692, DOI 10.1002/(SICI)1521-3765(19990604)5:6<1692::AID-CHEM1692>3.0.CO

[8]

2-M

[9] Asymmetric synthesis of α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines [J].

Cogan, DA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :268-269

[10] A concise update on the applications of chiral ferrocenyl phosphines in homogeneous catalysis leading to organic synthesis [J].

Colacot, TJ .

CHEMICAL REVIEWS, 2003, 103 (08) :3101-3118

← 1 2 3 4 5 6 7 →