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
收藏
页码：2543 / 2546
页数：4
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