Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michaelfaldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones

被引：20

作者：

Amireddy, Mamatha ^{[1
]}

Chen, Kwunmin ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 116, Taiwan

来源：

TETRAHEDRON | 2015年 / 71卷 / 42期

关键词：

Cascade reaction; Michael-aldol; 2-Arylideneindane-1; 3-diones; Squaramide-catalyst; gamma-Nitro ketones; HYDROGEN-BONDING ORGANOCATALYSTS; DOMINO REACTIONS; ENANTIOSELECTIVE SYNTHESIS; DIELS-ALDER; BENZOANNELATED CENTROPOLYQUINANES; SUBSTITUTED DISPIROCYCLOHEXANES; DIASTEREOSELECTIVE SYNTHESIS; ASYMMETRIC ORGANOCATALYSIS; MICHAEL/MICHAEL ADDITION; ANNULATION STRATEGY;

D O I：

10.1016/j.tet.2015.08.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between gamma-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20;1 dr and 86% ee). (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：8003 / 8008

页数：6

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