Enantioselective Synthesis of Succinimides by Michael Addition of 1,3-Dicarbonyl Compounds to Maleimides Catalyzed by a Chiral Bis(2-aminobenzimidazole) Organocatalyst

被引：37

作者：

Gomez-Torres, Eduardo ^{[1
,2
]}

Alonso, Diego A. ^{[1
,2
]}

Gomez-Bengoa, Enrique ^{[3
]}

Najera, Carmen ^{[1
,2
]}

机构：

[1] Univ Alicante, Dept Quim Organ, Alicante 03690, Spain

[2] Univ Alicante, Inst Sintesis Organ, Alicante 03690, Spain

[3] Univ Basque Country, Dept Quim Organ 1, San Sebastian 20080, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 2013卷 / 08期

关键词：

Asymmetric catalysis; Organocatalysis; Michael addition; Hydrogen bonds; Transition states; ASYMMETRIC CONJUGATE ADDITION; ALPHA-SUBSTITUTED CYANOACETATES; ALPHA; ALPHA-DISUBSTITUTED ALDEHYDES; BIFUNCTIONAL ORGANOCATALYSTS; BICYCLIC GUANIDINE; 1,4-ADDITION; DERIVATIVES; CARBON; ENTRY; ACIDS;

D O I：

10.1002/ejoc.201201046

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A wide variety of chiral succinimides have been prepared in high yields and enantioselectivities by asymmetric conjugate addition of 1,3-dicarbonyl compounds to maleimides under very mild reaction conditions using a bifunctional benzimidazole-derived organocatalyst. Computational and NMR studies support the hydrogen-bonding activation role of the catalyst and the origin of the stereoselectivity of the process.

引用

页码：1434 / 1440

页数：7

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