Highly Enantioselective Aza-Diels-Alder Reaction of 1-Azadienes with Enecarbamates Catalyzed by Chiral Phosphoric Acids

被引：80

作者：

He, Long ^{[1
]}

Laurent, Gregory ^{[1
]}

Retailleau, Pascal ^{[1
]}

Folleas, Benoit ^{[2
]}

Brayer, Jean-Louis ^{[2
]}

Masson, Geraldine ^{[1
]}

机构：

[1] CNRS, Inst Chim Subst Nat, Ctr Rech Gif, F-91198 Gif Sur Yvette, France

[2] ZAC Moulin, Diverchim, F-95700 Roissy En France, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 42期

关键词：

cycloaddition; dienes; heterocycles; organocatalysis; synthetic methods; BRONSTED ACID; POVAROV REACTION; GLYCOSIDASE INHIBITORS; 4-PI PARTICIPATION; ROOM-TEMPERATURE; ACTIVATION; 1-AZA-1,3-BUTADIENES; ALDEHYDES; ENAMIDES; ACCESS;

D O I：

10.1002/anie.201304969

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

On demand: A highly enantio- and diastereoselective synthesis of 6-amino- trisubstituted tetrahydropyridine compounds has been developed through the inverse-electron-demand aza-Diels-Alder reaction of N-aryl α,β- unsaturated ketimines with enecarbamates (E)-1. Chiral phosphoric acid catalysts achieve simultaneous activation of both the 1-azadiene and dienophile partners. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：11088 / 11091

页数：4

共 102 条

[1] Stronger bronsted acids
Akiyama, Takahiko
[J]. CHEMICAL REVIEWS, 2007, 107 (12) : 5744 - 5758
[2] Chiral Bronsted acid-catalyzed inverse electron-demand aza Diels-Alder reaction
Akiyama, Takahiko
Morita, Hisashi
Fuchibe, Kohei
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (40) : 13070 - 13071
[3] Recent progress in chiral Bronsted acid catalysis
Akiyama, Takahiko
Itoh, Junji
Fuchibe, Kohei
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) : 999 - 1010
[4] Highly Enantioselective Electrophilic α-Bromination of Enecarbamates: Chiral Phosphoric Acid and Calcium Phosphate Salt Catalysts
Alix, Aurelien
Lalli, Claudia
Retailleau, Pascal
Masson, Geraldine
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (25) : 10389 - 10392
[5] Enantioselective synthesis of piperidine, indolizidine, and quinolizidine alkaloids from a phenylglycinol-derived δ-lactam
Amat, M
Llor, N
Hidalgo, J
Escolano, C
Bosch, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (05) : 1919 - 1928
[6] [Anonymous], 2012, Angew. Chem
[7] [Anonymous], 2008, ANGEW CHEM
[8] Sugar-mimic glycosidase inhibitors: natural occurrence, biological activity and prospects for therapeutic application
Asano, N
Nash, RJ
Molyneux, RJ
Fleet, GWJ
[J]. TETRAHEDRON-ASYMMETRY, 2000, 11 (08) : 1645 - 1680
[9] Asymmetric routes to substituted piperidines
Bailey, PD
Millwood, PA
Smith, PD
[J]. CHEMICAL COMMUNICATIONS, 1998, (06) : 633 - 640
[10] Diels-Alder reactions of 1-azadienes
Behforouz, M
Ahmadian, M
[J]. TETRAHEDRON, 2000, 56 (30) : 5259 - 5288

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