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.

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收藏

页码：1377 / 1381

页数：5

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共 38 条

[21] Chiral amidomonophosphine-rhodium(I) catalyst for asymmetric 1,4-addition of arylboronic acids to cycloalkenones [J].

Kuriyama, M ;

Tomioka, K .

TETRAHEDRON LETTERS, 2001, 42 (05) :921-923

[22] C-H BOND ACTIVATION BY RUTHENIUM(0) COMPLEXES - ISOLATION OF AN ACTIVE INTERMEDIATE IN THE RUTHENIUM CATALYZED ALDOL AND MICHAEL REACTIONS [J].

MIZUHO, Y ;

KASUGA, N ;

KOMIYA, S .

CHEMISTRY LETTERS, 1991, (12) :2127-2130

[23] Deprotonation of organic compounds bearing acid protons promoted by metal amido complexes with chiral diamine ligands leading to new organometallic compounds [J].

Murata, K ;

Konishi, H ;

Ito, M ;

Ikariya, T .

ORGANOMETALLICS, 2002, 21 (02) :253-255

[24] Carbon-carbon bond forming reactions of N-bound transition metal α-cyanocarbanions:: a mechanistic probe for catalytic Michael reactions of nitriles [J].

Naota, T ;

Tannna, A ;

Murahashi, S .

CHEMICAL COMMUNICATIONS, 2001, (01) :63-64

[25] Metal-ligand bifunctional catalysis: A nonclassical mechanism for asymmetric hydrogen transfer between alcohols and carbonyl compounds [J].

Noyori, R ;

Yamakawa, M ;

Hashiguchi, S .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :7931-7944

[26] Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes [J].

Noyori, R ;

Hashiguchi, S .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (02) :97-102

[27] New strategies in organic catalysis: The first enantioselective organocatalytic Friedel-Crafts alkylation [J].

Paras, NA ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (18) :4370-4371

[28] New cobalt- and iron-catalyzed reactions of organozinc compounds [J].

Reddy, CK ;

Knochel, P .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (15) :1700-1701

[29] Asymmetric conjugate 1,4-addition of arylboronic acids to α,β-unsaturated esters catalyzed by rhodium(I)/(S)-binap [J].

Sakuma, S ;

Sakai, M ;

Itooka, R ;

Miyaura, N .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (19) :5951-5955

[30] Lanthanide complexes in multifunctional asymmetric catalysis [J].

Shibasaki, M ;

Yoshikawa, N .

CHEMICAL REVIEWS, 2002, 102 (06) :2187-2209

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