FACILE SEPARATION OF THE ENANTIOMERS OF DIETHYL N-(ARYL)-1-AMINO-1-ARYLMETHANEPHOSPHONATES ON A RATIONALLY DESIGNED CHIRAL STATIONARY-PHASE

Separation of the enantiomers of each member of a series of diethyl N- (aryl)-1-amino-1-arylmethanephosphonates is easily accomplished by HPL C using a WHELK-O column. This totally synthetic chiral stationary pha se (CSP 1) is designed to utilize specifiable interactions to differen tiate between enantiomers. The structural features of these phosphonat es suggested that CSP 1 would be applicable to the separation of the e nantiomers of this class of compounds even though there was an element of uncertainty owing to the presence of two pi-basic interaction site s, one on either side of the stereogenic center. The structures of the pi-basic N-aryl and C-aryl substituents have been varied, the structu re of the latter being found to have the greatest effect on retention and enantioselectivity.