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

ABSTRACT: 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 ?,?-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.

SUBMITTER: Torregrosa-Chinillach A

PROVIDER: S-EPMC6320823 | biostudies-other | 2018 Dec

REPOSITORIES: biostudies-other

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

Torregrosa-Chinillach Alejandro A Moragues Adrien A Pérez-Furundarena Haritz H Chinchilla Rafael R Gómez-Bengoa Enrique E Guillena Gabriela G

Molecules (Basel, Switzerland) 20181212 12

A primary amine-salicylamide derived from chiral <i>trans</i>-cyclohexane-1,2-diamine was used as an organocatalyst for the enantioselective conjugate addition of aldehydes, mainly α,α-disubstituted to <i>N</i>-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. ...[more]

PMID: 30545145

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