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Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide

1
Departamento de Química Orgánica, Facultad de Ciencias, and Instituto de Síntesis Orgánica (ISO), Uni­versidad de Alicante, Apdo. 99, 03080 Alicante, Spain
2
Departamento de Química Orgánica I, Universidad del País Vasco, Apdo. 1072, 20080 San Sebastián, Spain
*
Authors to whom correspondence should be addressed.
Molecules 2018, 23(12), 3299; https://doi.org/10.3390/molecules23123299
Received: 26 November 2018 / Revised: 5 December 2018 / Accepted: 9 December 2018 / Published: 12 December 2018
(This article belongs to the Section Organic Chemistry)
A primary amine-salicylamide derived from chiral trans-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to N-substituted maleimides. The reaction was performed in toluene as a solvent at room temperature. The corresponding enantioenriched adducts were obtained with high yields and enantioselectivities up to 94%. Theoretical calculations were used to justify the stereoinduction. View Full-Text
Keywords: organocatalysis; asymmetric synthesis; Michael addition; maleimides; aldehydes organocatalysis; asymmetric synthesis; Michael addition; maleimides; aldehydes
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MDPI and ACS Style

Torregrosa-Chinillach, A.; Moragues, A.; Pérez-Furundarena, H.; Chinchilla, R.; Gómez-Bengoa, E.; Guillena, G. Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide. Molecules 2018, 23, 3299.

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