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Direct Synthesis of ?-Thio Aromatic Acids from Aromatic Amino Acids.


ABSTRACT: Modified amino acids are useful synthetic components in both chemistry and biology. Here we describe a simple, scalable two-step procedure to generate ?-thio aromatic acids from aromatic amino acids with yields of up to 96%. Diazotization and ?-lactone mediated bromination efficiently form the ?-bromo acid with retention of configuration. Thiol substitution with mild reagents such as sodium hydrosulfide or sodium trithiocarbonate provides the inverted, free ?-thio acid. The mildly acidic soft nucleophile can then be utilized in many synthetic applications.

SUBMITTER: Samuels ER 

PROVIDER: S-EPMC6101259 | biostudies-literature | 2018 Mar

REPOSITORIES: biostudies-literature

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Direct Synthesis of α-Thio Aromatic Acids from Aromatic Amino Acids.

Samuels Eric R ER   Sevrioukova Irina I  

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]

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