Methodology for Synthesis of Enantiopure 3,5-Disubstituted Pyrrol-2-ones

Abstract

A new synthetic route towards chiral 3,5-disubstituted pyrrol-2-ones by starting from amino acids has been developed. The sequence features the conversion of amino acids into their corresponding alkynoic acid derivative followed by a Pd-catalyzed hydrostannylation of the triple bond and Stille cross-coupling reaction.

A series of lactam analogues of antifungal 3-(aryl)-5-hydroxymethyl-2,5-dihydrofuran-2-ones have thus been prepared.

Keywords

• Nitrogen heterocycles
• Amino acids
• Alkynes
• Chiral pool
• Green chemistry