Highly enantioselective aza-Diels-Alder reaction of 1-azadienes with enecarbamates catalyzed by chiral phosphoric acids

Angew Chem Int Ed Engl. 2013 Oct 11;52(42):11088-91. doi: 10.1002/anie.201304969. Epub 2013 Aug 28.

Abstract

On demand: A highly enantio- and diastereoselective synthesis of 6-amino- trisubstituted tetrahydropyridine compounds has been developed through the inverse-electron-demand aza-Diels-Alder reaction of N-aryl α,β-unsaturated ketimines with enecarbamates (E)-1. Chiral phosphoric acid catalysts achieve simultaneous activation of both the 1-azadiene and dienophile partners.

Keywords: cycloaddition; dienes; heterocycles; organocatalysis; synthetic methods.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aza Compounds / chemistry*
  • Carbamates / chemistry*
  • Catalysis
  • Molecular Structure
  • Phosphoric Acids / chemistry
  • Stereoisomerism

Substances

  • Aza Compounds
  • Carbamates
  • Phosphoric Acids
  • phosphoric acid