Title: Direct Synthesis of α-Thio Aromatic Acids from Aromatic Amino Acids.
Authors: Samuels, Eric R; Sevrioukova, Irina
Published In Tetrahedron Lett, (2018 Mar 21)
Abstract: Modified amino acids are useful synthetic components in both chemistry and biology. Here we describe a simple, scalable two-step procedure to generate α-thio aromatic acids from aromatic amino acids with yields of up to 96%. Diazotization and α-lactone mediated bromination efficiently form the α-bromo acid with retention of configuration. Thiol substitution with mild reagents such as sodium hydrosulfide or sodium trithiocarbonate provides the inverted, free α-thio acid. The mildly acidic soft nucleophile can then be utilized in many synthetic applications.
PubMed ID: 30140110
MeSH Terms: No MeSH terms associated with this publication