Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles

J Org Chem. 2015 Jul 2;80(13):6864-9. doi: 10.1021/acs.joc.5b00868. Epub 2015 Jun 12.

Abstract

A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity.

MeSH terms

  • Alkylation
  • Amino Acids / chemical synthesis*
  • Amino Acids / chemistry
  • Catalysis
  • Dioxanes / chemistry*
  • Molecular Structure
  • Nitriles / chemistry*
  • Protons
  • Stereoisomerism

Substances

  • 5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane
  • Amino Acids
  • Dioxanes
  • Nitriles
  • Protons