Organocatalytic enantioselective one-pot synthesis and application of substituted 1,4-dihydropyridines - Hantzsch Ester analogues

被引：70

作者：

Franke, Patrick T. ^{[1
]}

Johansen, Rasmus L. ^{[1
]}

Bertelsen, Soren ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Danish Natl Res Fdn Ctr Catalysis, Dept Chem, DK-8000 Aarhus C, Denmark

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2008年 / 3卷 / 02期

关键词：

asymmetric synthesis; multicomponent reactions; nitrogen heterocycles; organocatalysis; reduction;

D O I：

10.1002/asia.200700360

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An easy and simple one-pot approach for the formation of optically active substituted I.,4-dihydropyridines by using asymmetric organocatalysis is presented. The one-pot reaction of alpha,beta-unsaturated aldehydes with beta-diketones or beta-ketoesters and primary amines gives optically active 2,3-substituted 1,4-dihydropyridines in moderate yields and with enantioselectivities up to 95 % ee. It is also demonstrated that the optically active 1,4-dihydropyridines can be used in situ for the direct enantioselective reduction of, for example, alpha-ketoesters with high enantioselectivity.

引用

页码：216 / 224

页数：9

共 155 条

[61]

HAYASHI Y, 2007, ANGEW CHEM, V119, P5010

[62]

Hayashi Y., 2005, ANGEW CHEM, V117, P4284

[63] Diphenylprolinol silyl ether as a catalyst in an enantioselective, catalytic, tandem Michael/Henry reaction for the control of four stereocenters [J].

Hayashi, Yujiro ;

Okano, Tsubasa ;

Aratake, Seiji ;

Hazelard, Damien .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (26) :4922-4925

[64] Structure-activity relationships of first bishydroxymethyl-substituted cage dimeric 4-aryl-1,4-dihydropyridines as HIV-1 protease inhibitors [J].

Hilgeroth, A ;

Lilie, H .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2003, 38 (05) :495-499

[65] Dimeric 4-Aryl-1,4-Dihydropyridines: Development of a Third Class of Nonpeptidic HIV-1 Protease Inhibitors [J].

Hilgeroth, Andreas .

MINI-REVIEWS IN MEDICINAL CHEMISTRY, 2002, 2 (03) :235-245

[66] A powerful bronsted acid catalyst for the organocatalytic asymmetric transfer hydrogenation of imines [J].

Hoffmann, S ;

Seayad, AM ;

List, B .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (45) :7424-7427

[67]

Hoffmann S., 2005, ANGEW CHEM, V117, P7590, DOI [10.1002/ange.200503062, DOI 10.1002/ANGE.200503062]

[68] Catalytic asymmetric reductive amination of aldehydes via dynamic kinetic resolution [J].

Hoffmann, Sebastian ;

Nicoletti, Marcello ;

List, Benjamin .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) :13074-13075

[69]

HONG B, TETRAHEDRON, V63, P2840

[70] Organocatalytic asymmetric robinson annulation of α,β-unsaturated aldehydes:: Applications to the total synthesis of (+)-palitantin [J].

Hong, Bor-Cherng ;

Wu, Ming-Fun ;

Tseng, Hsing-Chang ;

Huang, Guo-Fong ;

Su, Cheng-Feng ;

Liao, Ju-Hsiou .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (22) :8459-8471

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