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Ji, Mi-Kyung,Hertsen, Dietmar,Yoon, Doo-Ha,Eum, Heesung,Goossens, Hannelore,Waroquier, Michel,Van Speybroeck, Veronique,D'hooghe, Matthias,De Kimpe, Norbert,Ha, Hyun-Joon Wiley (John WileySons) 2014 Chemistry - An Asian Journal Vol.9 No.4
<P>1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate was generated as a stable bicyclic aziridinium salt from the corresponding 2-(3-hydroxypropyl)aziridine upon reaction with p-toluenesulfonyl anhydride. This bicyclic aziridinium ion was then treated with various nucleophiles including halides, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening, mediated by the characteristics of the applied nucleophile. On the basis of DFT calculations, ring-opening reactions under thermodynamic control yield piperidines, whereas reactions under kinetic control can yield both piperidines and pyrrolidines depending on the activation energies for both pathways.</P>