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Publication Detail

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 Exiting the NIEHS site

MeSH Terms: No MeSH terms associated with this publication

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