Synthesis of Nitrile Equipped Unnatural Amino Acid Derivatives

Abstract

An entry into synthesis of β-nitrile equipped unnatural amino acid derivatives via nucleophilic addition of bromoacetonitrile or 2-bromopropanenitrile to α-imino esters or diimino esters is reported. The synthesis of nitrile containing β-amino alcohol, aspartic acid, and β-nitrile equipped N-arylated amino acids was achieved from nitrile containing α-amino esters obtained from this work. Dipeptide composed of nitrile attached unnatural α-amino acid and (R)-phenylalanine was also synthesized.