SYNTHESIS AND STEREOCHEMISTRY OF TRIFLUOROMETHYL-CONTAINING ISOXAZOLIDINES

Abstract

The reaction of trifluoromethyl-containing enones with hydroxylamine under various conditions is studied. The products in basic medium are equilibrating mixtures of isoxazolidine diastereomers in an ~1:1 ratio. The energy of the nitrogen atom inversion barrier in these compounds is 50-60 kJ/mol. Broadened signals are observed at room temperature in the ¹H and ¹³C NMR.

Authors: V. G. Nenajdenko, A. V. Sanin, O. L. Tok, and E. S. Balenkova.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (3), pp 348-357

http://link.springer.com/article/10.1007/BF02259367