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

The first successful enantioseparation of representative O,O ‐diphenyl‐ N ‐arylthioureidoalkylphosphonates, (±)‐Ptc‐Val P (OPh) 2 & (±)‐Ptc‐Leu P (OPh) 2 and thiourylenedi(isobutyl phosphonate), Tcm[Val P (OPh) 2 ] 2 on analytical and semipreparative scale was achieved by high‐performance liquid chromatography using polysaccharide‐based chiral stationary phases (CPs). Atc‐AA P (OPh) 2 was obtained using modified tricomponent condensations of the corresponding aldehydes, N ‐arylthiourea and triphenyl phosphite whereas Tcm[Val P (OPh) 2 ] 2 by the condensations of aldehydes, thiourea, and triphenyl phosphite. The prepared, racemic (±)‐Atc‐AA P (OPh) 2 [(±)‐Ptc‐Val P (OPh) 2 , (±)‐Ptc‐Leu P (OPh) 2 , (±)‐Ptc‐Pgly P (OPh) 2 and (±)‐Ntc‐Pgly P (OPh) 2 ] and racemic (±)‐Tcm[AA P (OPh) 2 ] 2 [(±)‐Tcm[Nva P (OPh) 2 ] 2 & (±)‐Tcm[Val P (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‐Val P (OPh) 2 , (±)‐Ptc‐Leu P (OPh) 2 and (±)‐Tcm[Val P (OPh) 2 ] 2 .