Organocatalytic Regio- and Stereoselective Inverse-Electron-Demand Aza-Diels-Alder Reaction of α,β-Unsaturated Aldehydes and N-Tosyl-1-aza-1,3-butadienes

被引：190

作者：

Han, Bo ^{[1
]}

He, Zhao-Quan ^{[1
]}

Li, Jun-Long ^{[1
]}

Li, Rui ^{[2
]}

Jiang, Kun ^{[1
]}

Liu, Tian-Yu ^{[1
]}

Chen, Ying-Chun ^{[1
,2
]}

机构：

[1] Sichuan Univ, W China Sch Pharm, Dept Med Chem, Key Lab Drug Targeting & Drug Delivery Syst Educ, Chengdu 610041, Peoples R China

[2] Sichuan Univ, W China Hosp, State Key Lab Biotherapy, Chengdu 610041, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2009年 / 48卷 / 30期

关键词：

asymmetric catalysis; aza-Diels-Alder reaction; dienamine catalysis; piperidines; alpha; beta-unsaturated aldehydes; DIPHENYLPROLINOL SILYL ETHER; ASYMMETRIC MICHAEL REACTION; 4-PI PARTICIPATION; 3+3 CYCLOADDITION; CATALYSIS; CASCADE; ACIDS; N-SULFONYL-1-AZA-1,3-BUTADIENES; 1-AZA-1,3-BUTADIENES; AMINOCATALYSIS;

D O I：

10.1002/anie.200902216

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Dienamines formed in situ from a chiral secondary amine and an α, β-unsaturated aldehyde undergo the highly α- regioselective title reaction to give densely functionalized piperidine derivatives with excellent enantioselectivity (see scheme). The products were converted into a variety of versatile cyclic frameworks. Ts=4-toluenesulfonyl. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5474 / 5477

页数：4

共 66 条

[51] Asymmetric enamine catalysis [J].

Mukherjee, Santanu ;

Yang, Jung Woon ;

Hoffmann, Sebastian ;

List, Benjamin .

CHEMICAL REVIEWS, 2007, 107 (12) :5471-5569

[52] Merging photoredox catalysis with organocatalysis: The direct asymmetric alkylation of aldehydes [J].

Nicewicz, David A. ;

MacMillan, David W. C. .

SCIENCE, 2008, 322 (5898) :77-80

[53]

Palomo C., 2006, ANGEW CHEM, V118, P8042

[54] Diarylprolinol ethers: Expanding the potential of enamine/iminium-ion catalysis [J].

Palomo, Claudio ;

Mielgo, Antonia .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :7876-7880

[55] Donor-acceptor-substituted cyclopropane derivatives and their application in organic synthesis [J].

Reissig, HU ;

Zimmer, R .

CHEMICAL REVIEWS, 2003, 103 (04) :1151-1196

[56]

Rubiralta M., 1991, Studies in Organic Chemistry, V43, P34, DOI 10.1016/B978-0-444-88348-3.50007-6

[57] BENZ[F]ISOQUINOLINE ANALOGS AS HIGH-AFFINITY SIGMA-LIGANDS [J].

RUSSELL, MGN ;

BAKER, R ;

BILLINGTON, DC ;

KNIGHT, AK ;

MIDDLEMISS, DN ;

NOBLE, AJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (11) :2025-2033

[58] Inverse-electron-demand hetero-Diels-Alder reaction of β,γ-unsaturated α-ketophosphonates catalyzed by prolinal dithioacetals [J].

Samanta, Sampak ;

Krause, Jonathan ;

Mandal, Tanmay ;

Zhao, Cong-Gui .

ORGANIC LETTERS, 2007, 9 (14) :2745-2748

[59] Total synthesis of piericidin A1 and B1 [J].

Schnermann, MJ ;

Boger, DL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (45) :15704-15705

[60]

Utsumi N., 2007, ANGEW CHEM, V119, P1910

← 1 2 3 4 5 6 7 →