Matthias Moens, N. De Kimpe*, M. D’hooghe
Jun 11, 2014
Citations
0
Influential Citations
36
Citations
Journal
The Journal of organic chemistry
Abstract
A convenient and stereoselective approach toward cis- and trans-1-alkyl-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines was developed starting from the corresponding α,α,α-trifluoroketones via imination, α-chlorination, and hydride-induced ring closure. The reactivity of these newly synthesized nonactivated α-CF3-aziridines was evaluated by applying N-protonation or N-alkylation to effect regio- and stereospecific aziridine ring opening by oxygen, halogen, sulfur, and nitrogen nucleophiles. Furthermore, nonactivated α-CF3-aziridines were easily transformed into their activated analogues by replacing the N-benzyl protecting group with a N-tosyl group, rendering these α-CF3-aziridines much more susceptible to nucleophilic ring opening.