The ring opening of 2-alkyl-substituted 1,1-di(arylmethyl)-and 1-methyl-1-(1-phenylethyl)aziridinium salts by fluoride, chloride, bromide and iodide in acetonitrile has been evaluated for the first time in a systematic way, affording regioisomeric mixtures of primary and secondary fluorides, whereas the corresponding secondary β-chloro, β-bromo and β-iodo amines were obtained as the sole reaction products through regiospecific ring opening at the substituted position. Both experimental and computational results revealed a product stability-dictated reaction outcome through thermodynamic control in the chloride, bromide and iodide case, involving rearrangement of the initially formed primary halides to the more stable secondary halides. The ring opening of the same aziridinium salts by fluoride, however, was shown to be mediated by steric interactions (kinetic control), furnishing the corresponding primary β-fluoro amines as the main reaction products. Only for 2-acylaziridinium ions, the reaction outcome was shown to be under full substrate control, affording secondary β-fluoro, β-chloro, β-bromo and β-iodo amines through exclusive attack at the activated -carbonyl carbon atom.
γT3 supplementation is effective in attenuating NAFLD and fibrosis through a synergistic mechanism of decreased DNL and hepatic ER stress. This work strongly supports the translational potential of γT3 supplementation against NAFLD.
The reaction of enantiomerically pure 2-substituted 1-phenylethyl-aziridine with methyl trifluoromethanesulfonate generated a stable methylaziridinium ion, which was reacted with various external nucleophiles, including nitrile, to yield synthetically valuable and optically pure acyclic amine derivatives in a completely regio- and stereoselective manner.
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