SEARCH

SEARCH BY CITATION

Keywords:

  • aminocatalysis;
  • computational chemistry;
  • heterocycles;
  • intermediate characterization;
  • NMR spectroscopy
Thumbnail image of graphical abstract

Pause and play: Dihydrooxazine oxides are stable intermediates that are protonated directly, without the intermediacy of the zwitterions, in organocatalytic Michael additions of aldehydes and nitroalkenes (see scheme, R=alkyl). Protonation of these species explains both the role of the acid co-catalyst in these reactions, and the observed stereochemistry when the reaction is conducted with α-alkylnitroalkenes.