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

Laboratorio de Organocatálisis Asimétrica, Departamento de Química Orgánica, Instituto de Síntesis Química y Catálisis Homogénea (ISQCH), CSIC-Universidad de Zaragoza, C/Pedro Cerbuna 12, E-50009 Zaragoza, Spain
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Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Derek J. McPhee
Molecules 2015, 20(9), 15807-15826; https://doi.org/10.3390/molecules200915807
Received: 17 July 2015 / Revised: 13 August 2015 / Accepted: 21 August 2015 / Published: 31 August 2015
(This article belongs to the Collection Recent Advances in Organocatalysis)
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. View Full-Text
Keywords: chiral base; enamine; isatylidene malononitrile; 1,4-dihydropyridine; enantioselective; isatin; organocatalysis; spirooxindole; 2-oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] chiral base; enamine; isatylidene malononitrile; 1,4-dihydropyridine; enantioselective; isatin; organocatalysis; spirooxindole; 2-oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)]
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MDPI and ACS Style

Auria-Luna, F.; Marqués-López, E.; Mohammadi, S.; Heiran, R.; Herrera, R.P. New Organocatalytic Asymmetric Synthesis of Highly Substituted Chiral 2-Oxospiro-[indole-3,4′- (1′,4′-dihydropyridine)] Derivatives. Molecules 2015, 20, 15807-15826.

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