1217710-80-9Relevant articles and documents
Nucleophile-dependent regio- and stereoselective ring opening of 1-azoniabicyclo[3.1.0]hexane tosylate
Ji, Mi-Kyung,Hertsen, Dietmar,Yoon, Doo-Ha,Eum, Heesung,Goossens, Hannelore,Waroquier, Michel,Vanspeybroeck, Veronique,D'Hooghe, Matthias,Dekimpe, Norbert,Ha, Hyun-Joon
, p. 1060 - 1067 (2014)
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. A ring thing: 1-[(1R)-(1-Phenylethyl)]-1-azoniabicyclo[3.1.0]hexane tosylate generated from 2-(3-hydroxypropyl)aziridine with p-toluenesulfonyl anhydride was treated with various nucleophiles including halide, azide, acetate, and cyanide in CH3CN to afford either piperidines or pyrrolidines through regio- and stereoselective ring opening (see scheme).