Asymmetric Organocatalytic Formal [2+2]-Cycloadditions via Bifunctional H-Bond Directing Dienamine Catalysis

被引：242

作者：

Albrecht, Lukasz ^{[1
]}

Dickmeiss, Gustav ^{[1
]}

Acosta, Fabio Cruz ^{[1
]}

Rodriguez-Escrich, Carles ^{[1
]}

Davis, Rebecca L. ^{[1
]}

Jorgensen, Karl Anker ^{[1
]}

机构：

[1] Aarhus Univ, Dept Chem, Ctr Catalysis, DK-8000 Aarhus C, Denmark

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 05期

关键词：

DIELS-ALDER REACTION; ALPHA; BETA-UNSATURATED ALDEHYDES; GAMMA-ALKYLATION; ACTIVATION;

D O I：

10.1021/ja211878x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new concept in organocatalysis allowing for the construction of cyclobutanes with four contiguous stereocenters with complete diastereo- and enantiomeric control by a formal [2 + 2]-cycloaddition is presented. The concept is based on simultaneous dual activation of alpha,beta-unsaturated aldehydes and nitroolefins by amino- and hydrogen-bonding catalysis, respectively. A new bifunctional squaramide-based aminocatalyst has been designed and synthesized in order to enable such an activation strategy. The potential and scope of the reaction are demonstrated, and computational studies which account for the stereochemical outcome are presented.

引用

页码：2543 / 2546

页数：4

共 30 条

[1] Squaramides: Bridging from Molecular Recognition to Bifunctional Organocatalysis
Aleman, Jose
Parra, Alejandro
Jiang, Hao
Jorgensen, Karl Anker
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (25) : 6890 - 6899
[2] Enantioselective organocatalysis using SOMO activation
Beeson, Teresa D.
Mastracchio, Anthony
Hong, Jun-Bae
Ashton, Kate
MacMillan, David W. C.
[J]. SCIENCE, 2007, 316 (5824) : 582 - 585
[3] Proline promoted synthesis of ring-fused homodimers:: Self-condensation of α,β-unsaturated aldehydes
Bench, Bennie J.
Liu, Chaomin
Evett, Colin R.
Watanabe, Coran M. H.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (25) : 9458 - 9463
[4] Cooperative Organocatalysis for the Asymmetric γ Alkylation of α-Branched Enals
Bergonzini, Giulia
Vera, Silvia
Melchiorre, Paolo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) : 9685 - 9688
[5] Dienamine catalysis:: Organocatalytic asymmetric γ-amination of α,β unsaturated aldehydes
Bertelsen, Slren
Marigo, Mauro
Brandes, Sebastian
Diner, Peter
Jorgensen, Karl Anker
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12973 - 12980
[6] Mechanistic Rationalization of Organocatalyzed Conjugate Addition of Linear Aldehydes to Nitro-olefins
Bures, Jordi
Armstrong, Alan
Blackmond, Donna G.
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (23) : 8822 - 8825
[7] Quantum Mechanical Investigations of Organocatalysis: Mechanisms, Reactivities, and Selectivities
Cheong, Paul Ha-Yeon
Legault, Claude Y.
Um, Joann M.
Celebi-Oelcuem, Nihan
Houk, K. N.
[J]. CHEMICAL REVIEWS, 2011, 111 (08) : 5042 - 5137
[8] Amine-catalyzed cyclizations of tethered α,β-unsaturated carbonyl compounds
de Figueiredo, Renata Marcia
Froehlich, Roland
Christmann, Mathias
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (08) : 1450 - 1453
[9] Bioactive cyclobutane-containing alkaloids
Dembitsky, Valery M.
[J]. JOURNAL OF NATURAL MEDICINES, 2008, 62 (01) : 1 - 33
[10] Dienamine Activation in the Organocatalytic Asymmetric Synthesis of cis-3,4-Difunctionalized Chromans and Dihydrocoumarins
Enders, Dieter
Yang, Xuena
Wang, Chuan
Raabe, Gerhard
Runsik, Jan
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (09) : 2255 - 2259

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