Versatile Intramolecular Aza-Prins and Prins Cyclization of Aryl Epoxides: A Facile Synthesis of Diaza-, Oxa-aza-, and Dioxa-bicycles

Abstract

Aryl epoxides undergo coupling smoothly with (E)-hex-3-ene-1,6-ditosylamide in the presence of 10 mol % p-TSA in 1,2-dichloroethane at 75 degrees C to produce the corresponding 1,5-ditosyl-octahydro-1H-pyrrolidino[3,2-c]pyridines in good yields with high trans-selectivity, whereas the coupling of (Z)-hex-3-ene-1,6-ditosylamide gave cis-fused octahydro-1H-pyrrolidino[3,2-c]pyridines predominantly. The use of readily available p-TSA makes this method simple, convenient, and practical.