Intramolecular S(N)2 reaction at α-carbon of trifluoromethyl group: Preparation of optically active 2-trifluoromethylaziridine

Article abstract of DOI:10.1016/S0957-4166(97)00320-0

We have succeeded in intramolecular nucleophilic substitution of the hydroxyl group in (S)-1-(alkylamino)-3,3,3-trifluoro-2-propanol. The reaction provides an optically pure (R)-1-benzyl-2-trifluoromethylaziridine in good yield from optically pure (S)-3-(benzylamino)-1,1,1-trifluoro-2-propanol which was prepared from (S)-3,3,3-trifluoropropene oxide (75% ee).