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Direct Synthesis of ?-Thio Aromatic Acids from Aromatic Amino Acids.
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ABSTRACT:
SUBMITTER: Samuels ER
PROVIDER: S-EPMC6101259 | biostudies-literature | 2018 Mar
REPOSITORIES: biostudies-literature
Publications
Direct Synthesis of α-Thio Aromatic Acids from Aromatic Amino Acids.
Tetrahedron letters 20180213 12
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 nu ...[more]
