Bifunctional transition metal-based molecular catalysts for asymmetric syntheses

被引：606

作者：

Ikariya, T

Murata, K

Noyori, R

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

[2] Nagoya Univ, Fac Sci, Dept Chem, Nagoya, Aichi 4648602, Japan

[3] Nagoya Univ, Res Ctr Mat Sci, Nagoya, Aichi 4648602, Japan

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2006年 / 4卷 / 03期

关键词：

D O I：

10.1039/b513564h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The discovery and development of conceptually new chiral bifunctional transition metal-based catalysts for asymmetric reactions is described. The chiral bifunctional Ru catalyst was originally developed for asymmetric transfer hydrogenation of ketones and imines and is now successfully applicable to enantioselective C-C bond formation reaction with a wide scope and high practicability. The deprotonation of 1,3-dicarbonyl compounds with the chiral amido Ru complexes leading to the amine Ru complexes bearing C- or O-bonded enolates, followed by further reactions with electrophlies gives C-C bond formation products. The present bifunctional Ru catalyst offers a great opportunity to open up new fundamentals for stereoselective molecular transformation including enantioselective C-H and C-C as well as C-O, C-N bond formation.

引用

收藏

页码：393 / 406

页数：14

相关论文

共 143 条

[41] Direct generation of nucleophilic chiral palladium enolate from 1,3-dicarbonyl compounds: Catalytic enantioselective Michael reaction with enones [J].

Hamashima, Y ;

Hotta, D ;

Sodeoka, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (38) :11240-11241

[42]

Hannedouche J, 2002, SYNLETT, P263

[43] SYNTHESIS AND CHEMISTRY OF RUTHENIUM HYDRIDO ARYLOXIDES AND ARYLAMIDES - AN INVESTIGATION OF STRUCTURE, N-H AND O-H ELIMINATION PROCESSES, PROTON-CATALYZED EXCHANGE-REACTIONS, AND RELATIVE RU-X BOND STRENGTHS [J].

HARTWIG, JF ;

ANDERSEN, RA ;

BERGMAN, RG .

ORGANOMETALLICS, 1991, 10 (06) :1875-1887

[44] SYNTHESIS OF (PME3)4RU(ME)(OC(CH2)ME) AS AN EQUILIBRIUM MIXTURE OF OXYGEN-BOUND AND CARBON-BOUND TRANSITION-METAL ENOLATES - THERMAL ELIMINATION OF METHANE TO FORM AN ETA-4-OXATRIMETHYLENEMETHANE COMPLEX [J].

HARTWIG, JF ;

ANDERSEN, RA ;

BERGMAN, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5670-5671

[45] ASYMMETRIC TRANSFER HYDROGENATION OF AROMATIC KETONES CATALYZED BY CHIRAL RUTHENIUM(II) COMPLEXES [J].

HASHIGUCHI, S ;

FUJII, A ;

TAKEHARA, J ;

IKARIYA, T ;

NOYORI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (28) :7562-7563

[46] Kinetic resolution of racemic secondary alcohols by Ru-II-catalyzed hydrogen transfer [J].

Hashiguchi, S ;

Fujii, A ;

Haack, KJ ;

Matsumura, K ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (03) :288-290

[47] Catalytic cycle of rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids.: Arylrhodium, oxa-π-allylrhodium, and hydroxorhodium intermediates [J].

Hayashi, T ;

Takahashi, M ;

Takaya, Y ;

Ogasawara, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (18) :5052-5058

[48]

Hayashi T, 2001, SYNLETT, P879

[49] Rhodium-catalyzed asymmetric 1,4-addition and its related asymmetric reactions [J].

Hayashi, T ;

Yamasaki, K .

CHEMICAL REVIEWS, 2003, 103 (08) :2829-2844

[50] Transfer hydrogenation of a variety of ketones catalyzed by rhodium complexes in aqueous solution and their application to asymmetric reduction using chiral Schiff base ligands [J].

Himeda, Y ;

Onozawa-Komatsuzaki, N ;

Sugihara, H ;

Arakawa, H ;

Kasuga, K .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2003, 195 (1-2) :95-100

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