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

[1] New strategies for organic catalysis: The first highly enantioselective organocatalytic Diels-Alder reaction [J].

Ahrendt, KA ;

Borths, CJ ;

MacMillan, DWC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) :4243-4244

[2] A novel use of Grubbs' carbene. Application to the catalytic deprotection of tertiary allylamines [J].

Alcaide, B ;

Almendros, P ;

Alonso, JM ;

Aly, MF .

ORGANIC LETTERS, 2001, 3 (23) :3781-3784

[3] SYNTHESIS OF 2,6-DISUBSTITUTED PIPERIDINES, OXANES, AND THIANES [J].

BALIAH, V ;

JEYARAMAN, R ;

CHANDRASEKARAN, L .

CHEMICAL REVIEWS, 1983, 83 (04) :379-423

[4] Enantioselective synthesis of highly functionalized 4-piperidones by the asymmetric imino-diels-alder reaction of chiral 2-amino-1,3-butadienes [J].

Barluenga, J ;

Aznar, F ;

Ribas, C ;

Valdes, C ;

Fernandez, M ;

Cabal, MP ;

Trujillo, J .

CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (07) :805-811

[5] STEREOSELECTIVE SYNTHESIS OF 4-PIPERIDONE AND 4-AMINOTETRAHYDROPYRIDINE DERIVATIVES BY THE IMINO DIELS-ALDER REACTION OF 2-AMINO-1,3-BUTADIENES [J].

BARLUENGA, J ;

AZNAR, F ;

VALDES, C ;

CABAL, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (12) :3391-3396

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

Betancort, JM ;

Barbas, CF .

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

[7] Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].

Betancort, JM ;

Sakthivel, K ;

Thayumanavan, R ;

Barbas, CF .

TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444

[8]

BIGELOW LA, ORGANIC SYNTHESES CO, V1, P80

[9] Direct catalytic asymmetric aldol reactions of aldehydes [J].

Bogevig, A ;

Kumaragurubaran, N ;

Jorgensen, KA .

CHEMICAL COMMUNICATIONS, 2002, (06) :620-621

[10]

Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO

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