The Strecker reaction coupled to Viedma ripening: a simple route to highly hindered enantiomerically pure amino acids

Chem Commun (Camb). 2018 Sep 25;54(77):10832-10834. doi: 10.1039/c8cc06658b.

Abstract

The Strecker reaction is broadly used for the preparation of α-amino acids. However, control of enantioselectivity remains challenging. We here couple the Strecker reaction to Viedma ripening for the absolute asymmetric synthesis of highly sterically hindered α-amino acids. As proof-of-principle, the enantiomerically pure α-amino acids tert-leucine and α-(1-adamantyl)glycine were obtained.

MeSH terms

  • Glycine / analogs & derivatives*
  • Glycine / chemistry*
  • Glycine / isolation & purification
  • Leucine / analogs & derivatives
  • Molecular Structure
  • Stereoisomerism
  • Valine / analogs & derivatives*
  • Valine / chemistry
  • Valine / isolation & purification

Substances

  • 2-amino-3,3-dimethylbutanoic acid
  • Leucine
  • Valine
  • Glycine