Molecules (Dec 2018)

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

  • Alejandro Torregrosa-Chinillach,
  • Adrien Moragues,
  • Haritz Pérez-Furundarena,
  • Rafael Chinchilla,
  • Enrique Gómez-Bengoa,
  • Gabriela Guillena

DOI
https://doi.org/10.3390/molecules23123299
Journal volume & issue
Vol. 23, no. 12
p. 3299

Abstract

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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.

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