Asymmetric 1,4-addition of β-keto esters to cyclic enones catalyzed by Ru amido complexes

被引：34

作者：

Wang, H

Watanabe, M

Ikariya, T ^{[1
]}

机构：

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

[2] Frontier Collaborat Res Ctr, Meguro Ku, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 06期

关键词：

multifunctional catalyst; Ru amido complex; Michael reaction; asymmetric C-C bond formation;

D O I：

10.1016/j.tetlet.2004.12.026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Well-defined Ru amido complexes effected asymmetric Michael addition of beta-keto esters to 2-cyclopenten-l-one to give quantitatively the corresponding Michael adducts with excellent ee although with a 1:1 diastereomer ratio. The stereochemical outcome of the reaction was significantly influenced by the structures of the catalysts and the structures of the P-keto esters; the ee value reaching up to 97%. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：963 / 966

页数：4

相关论文

共 22 条

[1] TUNGSTEN AND MOLYBDENUM 2-OXAALLYL (ETA-1-(C)-ENOLATE) COMPLEXES - FUNCTIONAL-GROUP TRANSFORMATIONS, PHOTOCHEMICAL ALDOL REACTIONS, AND ALKYNE/CO MIGRATORY INSERTION REACTIONS [J].

BURKHARDT, ER ;

DONEY, JJ ;

BERGMAN, RG ;

HEATHCOCK, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2022-2039

[2]

Christoffers J, 2000, EUR J ORG CHEM, V2000, P701, DOI 10.1002/(SICI)1099-0690(200003)2000:5<701::AID-EJOC701>3.0.CO

[3]

2-5

[4] Palladium-catalyzed α-arylation of carbonyl compounds and nitriles [J].

Culkin, DA ;

Hartwig, JF .

ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :234-245

[5] The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones [J].

Haack, KJ ;

Hashiguchi, S ;

Fujii, A ;

Ikariya, T ;

Noyori, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (03) :285-288

[6] 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

[7] 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

[8] 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

[9] Asymmetric Michael reactions of α-substituted acetates with cyclic enones catalyzed by multifunctional chiral Ru amido complexes [J].

Ikariya, T ;

Wang, H ;

Watanabe, M ;

Murata, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2004, 689 (08) :1377-1381

[10] ASYMMETRIC HYDROGENATION OF METHYL-(Z)-ALPHA-ACETAMIDOCINNAMATE CATALYZED BY (1,2-BIS((PHENYL-ORTHO-ANISOYL)PHOSPHINO)ETHANE)RHODIUM(I) - KINETICS, MECHANISM, AND ORIGIN OF ENANTIOSELECTION [J].

LANDIS, CR ;

HALPERN, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (06) :1746-1754