SEARCH

SEARCH BY CITATION

Keywords:

  • asymmetric catalysis;
  • cycloaddition;
  • 2,4-dienals;
  • enantioselectivity;
  • trienamine catalysis
Thumbnail image of graphical abstract

Raising the HOMO: 2,4-Dienals can react with nitroalkenes in trienamine-catalyzed asymmetric Diels–Alder reactions (see scheme). Crucial for the success is raising the HOMO energy of the diene through the introduction of appropriate substituents. The reaction exhibits unusually high enantioselectivity and exo selectivity; endo addition is possibly disfavored because of the electrostatic repulsion shown in the scheme.