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

[1] Mechanism of the hydrogenation of ketones catalyzed by trans-dihydrido(diamine)ruthenium(II) complexes [J].

Abdur-Rashid, K ;

Clapham, SE ;

Hadzovic, A ;

Harvey, JN ;

Lough, AJ ;

Morris, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (50) :15104-15118

[2]

Alexakis A, 2002, EUR J ORG CHEM, V2002, P3221

[3] Theory of asymmetric organocatalysis of aldol and related reactions: Rationalizations and predictions [J].

Allemann, C ;

Gordillo, R ;

Clemente, FR ;

Cheong, PHY ;

Houk, KN .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :558-569

[4] Ru(arene)(amino alcohol)-catalyzed transfer hydrogenation of ketones: Mechanism and origin of enantioselectivity [J].

Alonso, DA ;

Brandt, P ;

Nordin, SJM ;

Andersson, PG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (41) :9580-9588

[5] CRYSTAL-STRUCTURE AND REACTIVITY OF [RU(C6H4(NH)2-1,2)-(PPH3)3] WITH PI-ACID LIGANDS [J].

ANILLO, A ;

BARRIO, C ;

GARCIAGRANDA, S ;

OBESOROSETE, R .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1993, (07) :1125-1130

[6]

[Anonymous], 2000, CATALYTIC ASYMMETRIC

[7] Self-assembly of heterobimetallic complexes and reactive nucleophiles: A general strategy for the activation of asymmetric reactions promoted by heterobimetallic catalysts [J].

Arai, T ;

Yamada, YMA ;

Yamamoto, N ;

Sasai, H ;

Shibasaki, M .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (11) :1368-1372

[8] A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].

Arai, T ;

Sasai, H ;

Aoe, K ;

Okamura, K ;

Date, T ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106

[9] Development of a catalytic enantioselective conjugate addition of 1,3-dicarbonyl compounds to nitroalkenes for the synthesis of endothelin-A antagonist ABT-546. Scope, mechanism, and further application to the synthesis of the antidepressant rolipram [J].

Barnes, DM ;

Ji, JG ;

Fickes, MG ;

Fitzgerald, MA ;

King, SA ;

Morton, HE ;

Plagge, FA ;

Preskill, M ;

Wagaw, SH ;

Wittenberger, SJ ;

Zhang, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (44) :13097-13105

[10]

Berner OM, 2002, EUR J ORG CHEM, V2002, P1877

← 1 2 3 4 5 6 7 8 9 10 →