Versatile Intramolecular Aza-Prins and Prins Cyclization of Aryl Epoxides: A Facile Synthesis of Diaza-, Oxa-aza-, and Dioxa-bicycles
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posted on 2010-03-19, 00:00 authored by Jillu S. Yadav, Prashant Borkar, P. Pawan Chakravarthy, Basi V. Subba Reddy, Akella V. S. Sarma, Shaik Jeelani Basha, Balasubramanian Sridhar, René GréeAryl 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 °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.
