Catalytic activation of nucleophile precursors with metal acetates in alcohol media and applications to enantioselective Michael addition reactions

被引：12

作者：

Ono, Fumiyasu ^{[1
]}

Hasegawa, Masayuki ^{[1
]}

Kanemasa, Shuji ^{[1
]}

Tanaka, Junji ^{[1
]}

机构：

[1] Kyushu Univ, Inst Mat Sci & Engn, Kasuga, Fukuoka 8168580, Japan

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 34期

关键词：

D O I：

10.1016/j.tetlet.2008.05.153

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Nickel(II) acetate tetrahydrate works as catalyst to activate nucleophile precursors in Michael addition reactions. Use of alcohol media is essential for the high catalytic activation of nucleophile precursors. Catalytic enantioselective reactions using a chiral nickel(II) acetate tetrahydrate between dimedone and alpha,beta-unsaturated amide acceptors provide a useful synthetic access to enantiomers of enol lactones through the carbon-carbon bond formation. (c) 2008 Elsevier Ltd. All rights reserved.

引用

收藏

页码：5105 / 5107

页数：3

相关论文

共 20 条

[1] A SPECTACULAR EXAMPLE OF THE IMPORTANCE OF ROTATIONAL BARRIERS - THE IONIZATION OF MELDRUMS ACID [J].

ARNETT, EM ;

HARRELSON, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :809-812

[2] Synthesis and aldol reactivity of O- and C-enolate complexes of nickel [J].

Cámpora, J ;

Maya, CM ;

Palma, P ;

Carmona, E ;

Gutiérrez-Puebla, E ;

Ruiz, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (06) :1482-1483

[3] Formation of quaternary stereocenters by copper-catalyzed Michael reactions with L-valine amides as auxiliaries [J].

Christoffers, J .

CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (20) :4862-4867

[4]

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

[5]

2-5

[6] Recent advances in metal-catalyzed asymmetric conjugate additions [J].

Christoffers, Jens ;

Koripelly, Girish ;

Rosiak, Anna ;

Roessle, Michael .

SYNTHESIS-STUTTGART, 2007, (09) :1279-1300

[7] Ni(II) Tol-BINAP-catalyzed enantioselective orthoester alkylations of N-acylthiazolidinethiones [J].

Evans, DA ;

Thomson, RJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) :10506-10507

[8] Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].

Evans, DA ;

Seidel, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9958-9959

[9] Ni(II) Tol-BINAP-catalyzed enantioselective Michael reactions of β-ketoesters and unsaturated N-acylthiazolidinethiones [J].

Evans, DA ;

Thomson, RJ ;

Franco, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (31) :10816-10817

[10] A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction [J].

Evans, DA ;

Seidel, D ;

Rueping, M ;

Lam, HW ;

Shaw, JT ;

Downey, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) :12692-12693