title: Enantiomerically pure 2-aryl(alkyl)-2-trifluoromethylaziridines: synthesis and ring opening with selected O- and N-nucleophiles.
abstract: We report herein the synthesis of enantiomerically pure 2-phenyl- and 2-ethyl-2-trifluoromethylaziridines by Mitsunobu-type cyclisation of the corresponding N-protected amino alcohols, and our results regarding their ring opening with selected nucleophiles. Under basic conditions, N-tosyl aziridines have been regioselectively opened at the less hindered carbon. Under acidic conditions, the regioselectivity of the attack depends on the nature of the substituent at C-2 and on the nitrogen protecting group.
authors.affiliation: Université de Reims-Champagne-Ardenne, Institut de Chimie Moléculaire de Reims, UMR CNRS 6229, UFR des Sciences Exactes et Naturelles, BP 1039, 51687 Reims cedex 2, France. fabienne.grellepois@univ-reims.fr
authors.forename: Fabienne
authors.initials: F
authors.lastname: Grellepois
authors.forename: Jean
authors.initials: J
authors.lastname: Nonnenmacher
authors.forename: Fabien
authors.initials: F
authors.lastname: Lachaud
authors.forename: Charles
authors.initials: C
authors.lastname: Portella
mesh_terms: D000478:Alkylation; D001388:Aziridines / Q000138:chemical synthesis*; D017611:Fluorine Compounds / Q000138:chemical synthesis*; D006868:Hydrolysis; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001388:Aziridines; D017611:Fluorine Compounds; C031132:propyleneimine