Optical Resolution of Dimethyl alpha-Hydroxy-Arylmethylphosphonates via Diastereomer Complex Formation Using Calcium Hydrogen O,O '-Dibenzoyl-(2R,3R)-Tartrate;X-Ray Analysis of the Complexes and Products

Radai, Zita; Bagi, Peter; Czugler, Matyas; Karaghiosoff, Konstantin und Keglevich, Gyorgy (2020): Optical Resolution of Dimethyl alpha-Hydroxy-Arylmethylphosphonates via Diastereomer Complex Formation Using Calcium Hydrogen O,O '-Dibenzoyl-(2R,3R)-Tartrate;X-Ray Analysis of the Complexes and Products. In: Symmetry-Basel, Bd. 12, Nr. 5, 758

Abstract

Two dimethyl alpha -hydroxy-arylmethylphosphonates (aryl = Ph and 2-MeOPh) were subjected to optical resolution via diastereomer complex formation applying the acidic calcium salt of O,O ' -dibenzoyl-(2R,3R)-tartaric acid as the resolving agent. The dominating diastereomer complexes, whose structure was determined by single crystal X-ray measurements, were obtained in 96% and 68% diastereomer excess values, respectively. After decomposing the diastereomer formations by extraction, and after recrystallizations, the major enantiomer (S and R, respectively) of the alpha -hydroxyphosphonates were prepared in enantiomeric excess values of 96% and 68%, respectively. The stereostructure of the two alpha -hydroxy-arylmethylphosphonates was again established by X-ray measurements. Detailed study on the X-ray data allowed valuable conclusions on the nature of the coordination in the complexes (intermolecular interactions), and on the H-bonding.

• Dokumententyp: Zeitschriftenartikel
• Fakultät: Chemie und Pharmazie > Department Chemie
• Themengebiete: 500 Naturwissenschaften und Mathematik > 540 Chemie
• Sprache: Englisch