Synthesis and enzymatic resolution of novel analogs of alicyclic and heterocyclic mandelic acid derivatives

Abstract

Synthesis and enzymatic resolution of a new class of alicyclic and heterocyclic mandelic acid derivatives was described. The method relied on the preparation of cyanohydrins from the commercially available aldehydes followed by hydrolysis to corresponding racemic hydroxy esters that were used in the resolution with the Amano PS enzyme. An alternative approach was proposed for compounds that were not suitable for this procedure. For the selected examples, synthesis of the corresponding mandelic acid analogs using the subsequent hydrolysis of esters followed by enantiomeric enrichment via recrystallization of the diastereomeric salt was performed.