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.
STUDIES TOWARD A MODEL FOR PREDICTING THE DIASTEREOSELECTIVITY IN THE ELECTROPHILIC AMINATION OF CHIRAL 1,3,2-OXAZAPHOSPHOLANES / G. JOMMI, G. MIGLIERINI, R. PAGLIARIN, G. SELLO, M. SISTI. - In: TETRAHEDRON. - ISSN 0040-4020. - 48:35(1992), pp. 7275-7288.
STUDIES TOWARD A MODEL FOR PREDICTING THE DIASTEREOSELECTIVITY IN THE ELECTROPHILIC AMINATION OF CHIRAL 1,3,2-OXAZAPHOSPHOLANES
R. PAGLIARIN;G. SELLO;
1992
Abstract
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.
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