Amino Acid Sulfinate Salts as Alkyl Radical Precursors

A general approach to the synthesis of amino acid sulfinate salts from commercially available alpha-chiral hydroxylated amino acids is reported. These reagents are shown to be valuable precursors to alkyl radicals under mild photochemical oxidation conditions. The photochemically generated amino acid radicals engage readily with alkyl and aryl disulfide radical traps to afford a diverse suite of modified amino acids.

Automated summary

A method for synthesizing amino acid sulfinate salts from commercially available alpha-chiral hydroxylated amino acids is presented. These reagents can serve as valuable precursors to alkyl radicals through mild photochemical oxidation. The resulting amino acid radicals readily react with alkyl and aryl disulfide radical traps, yielding a diverse range of modified amino acids.