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High‐performance liquid chromatographic enantioseparation of N ‐aryl‐thioureidoalkylphosphonates and thiourylenedi(alkylphosphonates) on polysaccharide‐based chiral stationary phases
Author(s) -
Drabowicz Józef,
Kudzin Marcin H.,
Kudzin Zbigniew H.,
PokoraSobczak Patrycja
Publication year - 2018
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.22794
Subject(s) - chemistry , phosphonate , triphenyl phosphite , thiourea , high performance liquid chromatography , chromatography , enantiomer , aryl , stereochemistry , organic chemistry , alkyl
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 .