New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′-(1′,4′-dihydropyridine)] Derivatives

被引：29

作者：

Auria-Luna, Fernando ^{[1
]}

Marques-Lopez, Eugenia ^{[1
]}

Mohammadi, Somayeh ^{[1
]}

Heiran, Roghayeh ^{[1
]}

Herrera, Raquel P. ^{[1
]}

机构：

[1] Univ Zaragoza, CSIC, ISQCH, Lab Organocatalisis Asimetr,Dept Quim Organ, E-50009 Zaragoza, Spain

来源：

MOLECULES | 2015年 / 20卷 / 09期

关键词：

chiral base; enamine; isatylidene malononitrile; 1; 4-dihydropyridine; enantioselective; isatin; organocatalysis; spirooxindole; 2-oxospiro-[indole-3; 4-(1; 4-dihydropyridine); ENANTIOSELECTIVE MICHAEL ADDITION; QUATERNARY CARBON CENTERS; STRUCTURE-BASED DESIGN; ALPHA; BETA-UNSATURATED IMIDES; 1,3-DICARBONYL COMPOUNDS; MULTICOMPONENT SYNTHESIS; EFFICIENT SYNTHESIS; CONSTRUCTION; CHEMISTRY; ISATINS;

D O I：

10.3390/molecules200915807

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Herein, we report our preliminary results concerning the first promising asymmetric synthesis of highly functionalized 2-oxospiro-[indole-3,4-(1,4-dihydropyridine)] via the reaction of an enamine with isatylidene malononitrile derivatives in the presence of a chiral base organocatalyst. The moderate, but promising, enantioselectivity observed (30%-58% ee (enantiomeric excess)) opens the door to a new area of research for the asymmetric construction of these appealing spirooxindole skeletons, whose enantioselective syntheses are still very limited.

引用

页码：15807 / 15826

页数：20

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