Catalytic asymmetric synthesis of both enantiomers of 4‑substituted 1,4-dihydropyridines with the use of bifunctional thiourea-ammonium salts bearing different counterions

Molecules. 2010 Nov 15;15(11):8305-26. doi: 10.3390/molecules15118305.

Abstract

Organoammonium salts composed of a Brønsted acid and an anilinothiourea promoted the Michael addition of ß-keto esters and α,ß-unsaturated aldehydes in the presence of primary amines to give functionalized 1,4-dihydropyridines enantioselectively. With the use of the different Brønsted acids such as DFA and HBF(4) with the same bifunctional thiourea, both enantiomers of 4-substituted 1,4-dihydropyridine were synthesized from the same starting materials.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry*
  • Molecular Structure
  • Quaternary Ammonium Compounds / chemistry*
  • Stereoisomerism
  • Thiourea / chemistry*

Substances

  • Aldehydes
  • Dihydropyridines
  • Quaternary Ammonium Compounds
  • 1,4-dihydropyridine
  • Thiourea