Molecules, Vol. 23, Pages 3299: Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide

Molecules, Vol. 23, Pages 3299: Enantioselective Michael Addition of Aldehydes to Maleimides Organocatalyzed by a Chiral Primary Amine-Salicylamide
Molecules doi: 10.3390/molecules23123299
Authors:
Alejandro Torregrosa-Chinillach
Adrien Moragues
Haritz Pérez-Furundarena
Rafael Chinchilla
Enrique Gómez-Bengoa
Gabriela Guillena

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.

Source: Molecules - December 12, 2018 Category: Chemistry Authors: Alejandro Torregrosa-Chinillach Adrien Moragues Haritz P érez-Furundarena Rafael Chinchilla Enrique G ómez-Bengoa Gabriela Guillena Tags: Article Source Type: research