Proline-catalyzed imino-Diels-Alder reactions:: Synthesis of meso-2,6-diaryl-4-piperidones

被引：37

作者：

Aznar, Fernando ^{[1
]}

Garcia, Ana-Belen ^{[1
]}

Cabal, Maria-Paz ^{[1
]}

机构：

[1] Univ Oviedo, Inst Univ Quim Organomet Enrique Moles, E-33006 Oviedo, Spain

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2006年 / 348卷 / 16-17期

关键词：

2-amino-1,3-butadienes; meso-2,6-diaryl-4-piperidones; hetero-Diels-Alder reaction; nitrogen heterocycles; organic catalysis; L-proline;

D O I：

10.1002/ADSC.200600318

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Amine-catalyzed imino-Diels-Alder reactions of acyclic alpha,beta-unsaturated ketones with imines have been developed. L-Proline catalyzed the in situ generation of 2-amino-1,3-butadienes to provide a stereoselective synthesis of meso-2,6-diaryl-4-piperidones in one direct step.

引用

收藏

页码：2443 / 2448

页数：6

相关论文

共 55 条

[11]

2-Y

[12] Protonated chiral catalysts: Versatile tools for asymmetric synthesis [J].

Bolm, C ;

Rantanen, T ;

Schiffers, I ;

Zani, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (12) :1758-1763

[13] Recent developments in imino Diels-Alder reactions [J].

Buonora, P ;

Olsen, JC ;

Oh, T .

TETRAHEDRON, 2001, 57 (29) :6099-6138

[14] Ru(IV)-catalyzed isomerization of allylamines in water:: A highly efficient procedure for the deprotection of N-allylic amines [J].

Cadierno, V ;

García-Garrido, SE ;

Gimeno, J ;

Nebra, N .

CHEMICAL COMMUNICATIONS, 2005, (32) :4086-4088

[15] Organocatalytic asymmetric assembly reactions:: One-pot synthesis of functionalized β-amino alcohols from aldehydes, ketones, and azodicarboxylates [J].

Chowdari, NS ;

Ramachary, DB ;

Barbas, CF .

ORGANIC LETTERS, 2003, 5 (10) :1685-1688

[16] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].

Córdova, A ;

Watanabe, S ;

Tanaka, F ;

Notz, W ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867

[17] A highly enantioselective amino acid-catalyzed route to functionalized α-amino acids [J].

Córdova, A ;

Notz, W ;

Zhong, GF ;

Betancort, JM ;

Barbas, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1842-1843

[18]

Dalko PI, 2001, ANGEW CHEM INT EDIT, V40, P3726, DOI 10.1002/1521-3773(20011015)40:20<3726::AID-ANIE3726>3.0.CO

[19]

2-D

[20] In the golden age of organocatalysis [J].

Dalko, PI ;

Moisan, L .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (39) :5138-5175

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