Selective synthesis of cis- and trans-2-(methyl/phenyl)-3-(trifluoromethyl)aziridines and their regio- and stereospecific ring opening.
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.
SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University , Coupure Links 653, B-9000 Ghent, Belgium.
Matthias
M
Moens
Norbert
N
De Kimpe
Matthias
M
D'hooghe
D000478:Alkylation; D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D001388:Aziridines; D006843:Hydrocarbons, Chlorinated; C033132:aziridine