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Molecules 2017, 22(8), 1328; doi:10.3390/molecules22081328

Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions

1
Departamento de Química, Centro de Investigación y de Estudios Avanzados, Avenida IPN 2508, Ciudad de México 07360, Mexico
2
El Colegio Nacional, Luis González Obregón 23, Centro Histórico, Ciudad de México 06020, Mexico
*
Author to whom correspondence should be addressed.
Received: 7 June 2017 / Revised: 24 July 2017 / Accepted: 27 July 2017 / Published: 10 August 2017
(This article belongs to the Collection Recent Advances in Organocatalysis)
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Abstract

The application of six novel α,β-dipeptides as chiral organocatalysts in the asymmetric Michael addition reaction between enolizable aldehydes and N-arylmaleimides or nitroolefins is described. With N-arylmaleimides as substrates, the best results were achieved with dipeptide 2 as a catalyst in the presence of aq. NaOH. Whereas dipeptides 4 and 6 in conjunction with 4-dimethylaminopyridine (DMAP) and thiourea as a hydrogen bond donor proved to be highly efficient organocatalytic systems in the enantioselective reaction between isobutyraldehyde and various nitroolefins. View Full-Text
Keywords: peptides; Michael addition; asymmetric organocatalysis; solvent-free reactions peptides; Michael addition; asymmetric organocatalysis; solvent-free reactions
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Avila-Ortiz, C.G.; Díaz-Corona, L.; Jiménez-González, E.; Juaristi, E. Asymmetric Michael Addition Organocatalyzed by α,β-Dipeptides under Solvent-Free Reaction Conditions. Molecules 2017, 22, 1328.

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