High-performance liquid chromatographic enantioseparation of N-aryl-thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide-based chiral stationary phases.

Abstract

The first successful enantioseparation of representative O,O-diphenyl-N-arylthioureidoalkylphosphonates, (±)-Ptc-ValP (OPh)2 & (±)-Ptc-LeuP (OPh)2 and thiourylenedi(isobutyl phosphonate), Tcm[ValP (OPh)2 ]2 on analytical and semipreparative scale was achieved by high-performance liquid chromatography using polysaccharide-based chiral stationary phases (CPs). Atc-AAP (OPh)2 was obtained using modified tricomponent condensations of the corresponding aldehydes, N-arylthiourea and triphenyl phosphite whereas Tcm[ValP (OPh)2 ]2 by the condensations of aldehydes, thiourea, and triphenyl phosphite. The prepared, racemic (±)-Atc-AAP (OPh)2 [(±)-Ptc-ValP (OPh)2 , (±)-Ptc-LeuP (OPh)2 , (±)-Ptc-PglyP (OPh)2 and (±)-Ntc-PglyP (OPh)2 ] and racemic (±)-Tcm[AAP (OPh)2 ]2 [(±)-Tcm[NvaP (OPh)2 ]2 & (±)-Tcm[ValP (OPh)2 ]2 ] were adequately characterized and used for chromatographic separations on high-performance liquid chromatography-chiral stationary phases. The best results were obtained for (±)-Ptc-ValP (OPh)2 , (±)-Ptc-LeuP (OPh)2 and (±)-Tcm[ValP (OPh)2 ]2 .