Asymmetric Michael reactions of α-substituted acetates with cyclic enones catalyzed by multifunctional chiral Ru amido complexes

被引：41

作者：

Ikariya, T

Wang, H

Watanabe, M

Murata, K

机构：

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

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

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2004年 / 689卷 / 08期

关键词：

multifunction; Ru amido complex; Michael reaction; asymmetric; C-C bond formation;

D O I：

10.1016/j.jorganchem.2003.12.002

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Well-defined 16-electron chiral Ru amido complexes, Ru[(R,R)-diamine](eta(6)-arene), efficiently catalyze asymmetric Michael additions of Michael donors to cyclic enones to give adducts in high yields and with excellent ees. beta-Ketoesters or nitroacetate as Michael donors react with 2-cyclopentenone in toluene or t-butyl alcohol containing the Ru amido catalyst (S/C = 50) to afford the Michael adduct in 99% yield and with up to 92% ee. The outcome of the reaction was delicately influenced by the structures of the diamine and arene ligands as well as reaction conditions. (C) 2003 Elsevier B.V. All rights reserved.

引用

收藏

页码：1377 / 1381

页数：5

相关论文

共 38 条

[1] Tandem enantioselective conjugate addition-cyclopropanation. Application to natural products synthesis [J].

Alexakis, A ;

March, S .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8753-8757

[2]

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

[3] 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

[4] Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].

Betancort, JM ;

Barbas, CF .

ORGANIC LETTERS, 2001, 3 (23) :3737-3740

[5] (+)-camphor-derived tri- and tetradentate amino alcohols; synthesis and application as ligands in the nickel catalyzed enantioselective conjugate addition of diethylzinc [J].

deVries, AHM ;

Imbos, R ;

Feringa, BL .

TETRAHEDRON-ASYMMETRY, 1997, 8 (09) :1467-1473

[6] Highly enantioselective catalytic conjugate addition and tandem conjugate addition - Aldol reactions of organozinc reagents [J].

Feringa, BL ;

Pineschi, M ;

Arnold, LA ;

Imbos, R ;

de Vries, AHM .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (23) :2620-2623

[7] 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

[8] 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

[9] 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

[10] A chiral chelating diene as a new type of chiral ligand for transition metal catalysts: Its preparation and use for the rhodium-catalyzed asymmetric 1,4-addition [J].

Hayashi, T ;

Ueyama, K ;

Tokunaga, N ;

Yoshida, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (38) :11508-11509

← 1 2 3 4 →