STUDIES TOWARD A MODEL FOR PREDICTING THE DIASTEREOSELECTIVITY IN THE ELECTROPHILIC AMINATION OF CHIRAL 1,3,2-OXAZAPHOSPHOLANES

A model. has been developed for predicting the diastereoselectivity in the electrophilic amination of chiral 1,3,2-oxazaphospholanes derived from ephedrine and pseudoephedrine derivatives. The influence of the five-membered ring conformations and of the bulkiness of the ring substituents has been deeply analyzed both for reactivity prediction and for H-1-NMR data interpretation. The theoretical and experimental results are in good agreement.