A stereochemically well-defined rhodium(III) catalyst for asymmetric transfer hydrogenation of ketones

被引：161

作者：

Matharu, DS

Morris, DJ

Kawamoto, AM

Clarkson, GJ

Wills, M ^{[1
]}

机构：

[1] Univ Warwick, Dept Chem, Asymmetr Catalysis Grp, Coventry CV4 7AL, W Midlands, England

[2] Univ Warwick, Dept Chem, Xray Crystallog Unit, Coventry CV4 7AL, W Midlands, England

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 24期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1021/ol052559f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A rhodium(III) catalyst for asymmetric transfer hydrogenation of ketones has been designed. The incorporation of a tethering group between the diamino group and the cyclopentadienyl unit provides extra stereochemical rigidity. The catalyst is capable of enantioselective reduction of a range of ketones in excellent ee using formic acid/triethylamine as both the solvent and the reducing agent.

引用

收藏

页码：5489 / 5491

页数：3

相关论文

共 30 条

[1]

Blacker J., 2004, ASYMMETRIC CATALYSIS, P201, DOI DOI 10.1002/3527602151.CH11

[2] Mechanisms of the H2-hydrogenation and transfer hydrogenation of polar bonds catalyzed by ruthenium hydride complexes [J].

Clapham, SE ;

Hadzovic, A ;

Morris, RH .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2201-2237

[3] A new class of Rh(III) catalyst containing an aminoalcohol tethered to a tetramethylcyclopentadienyl hydrogenation group for asymmetric transfer of ketones [J].

Cross, DJ ;

Houson, I ;

Kawamoto, AM ;

Wills, M .

TETRAHEDRON LETTERS, 2004, 45 (04) :843-846

[4] Rhodium versus ruthenium:: contrasting behaviour in the asymmetric transfer hydrogenation of α-substituted acetophenones [J].

Cross, DJ ;

Kenny, JA ;

Houson, I ;

Campbell, L ;

Walsgrove, T ;

Wills, M .

TETRAHEDRON-ASYMMETRY, 2001, 12 (12) :1801-1806

[5] The United Kingdom Chemical Database Service [J].

Fletcher, DA ;

McMeeking, RF ;

Parkin, D .

JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, 1996, 36 (04) :746-749

[6] Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture [J].

Fujii, A ;

Hashiguchi, S ;

Uematsu, N ;

Ikariya, T ;

Noyori, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2521-2522

[7] Asymmetric transfer hydrogenation of α-aminoalkyl α′-chloromethyl ketones with chiral Rh complexes [J].

Hamada, T ;

Torii, T ;

Onishi, T ;

Izawa, K ;

Ikariya, T .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (21) :7391-7394

[8] A practical synthesis of optically active aromatic epoxides via asymmetric transfer hydrogenation of α-chlorinated ketones with chiral rhodium-diamine catalyst [J].

Hamada, T ;

Torii, T ;

Izawa, K ;

Ikariya, T .

TETRAHEDRON, 2004, 60 (34) :7411-7417

[9] Practical synthesis of optically active styrene oxides via reductive transformation of 2-chloroacetophenones with chiral rhodium catalysts [J].

Hamada, T ;

Torii, T ;

Izawa, K ;

Noyori, R ;

Ikariya, T .

ORGANIC LETTERS, 2002, 4 (24) :4373-4376

[10] A new class of "tethered" ruthenium(II) catalyst for asymmetric transfer hydrogenation reactions [J].

Hannedouche, J ;

Clarkson, GJ ;

Wills, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (04) :986-987