Organocatalytic Asymmetric Conjugate Addition of Aldehydes to Maleimides and Nitroalkenes in Deep Eutectic Solvents

Molecules. 2019 Nov 9;24(22):4058. doi: 10.3390/molecules24224058.

Abstract

A chiral primary amine-salicylamide is used as an organocatalyst for the enantioselective conjugate addition of α,α-disubstituted aldehydes to maleimides and nitroalkenes. The reactions are performed in deep eutectic solvents as reaction media at room temperature, leading to the corresponding adducts with enantioselectivities up to 88% (for maleimides) and 80% (for nitroalkenes). Catalyst and solvent can be recovered and reused.

Keywords: conjugate addition; deep eutectic solvents; maleimides; nitroalkenes; organocatalysis.

MeSH terms

  • Alkenes / chemistry*
  • Amines / chemistry
  • Catalysis
  • Maleimides / chemistry*
  • Nitro Compounds / chemistry*
  • Salicylamides / chemistry
  • Solvents / chemistry*

Substances

  • Alkenes
  • Amines
  • Maleimides
  • Nitro Compounds
  • Salicylamides
  • Solvents
  • salicylamide