RESOLUTION AND DETERMINATION OF THE ENANTIOMERIC PURITY AND ABSOLUTE-CONFIGURATIONS OF ALPHA-ARYL-ALPHA-HYDROXYMETHANEPHOSPHONATES

The enantiomers of each of a series of alpha-aryl-alpha-hydroxymethane phosphonates have been found to be easily separable by liquid chromato graphy on a chiral stationary phase, CSP 1, and to elute in the order expected from mechanistic considerations. The dextro- enantiomer of ea ch of the compounds listed in Table 1 is preferentially retained by th e (3R, 4S)-WHELK-O 1 stationary phase and is assigned the (+)-(R)-conf iguration. The presence of an ortho- substituent interferes with the r ecognition process, reduces the separation factor for the enantiomers, and possibly alters their elution order. Copyright (C) 1996 Elsevier Science Ltd