Versatile intramolecular aza-Prins and Prins cyclization of aryl epoxides: a facile synthesis of diaza-, oxa-aza-, and dioxa-bicycles

Jillu S Yadav; Prashant Borkar; P Pawan Chakravarthy; Basi V Subba Reddy; Akella V S Sarma; Shaik Jeelani Basha; Balasubramanian Sridhar; René Grée

doi:10.1021/jo902683p

Versatile intramolecular aza-Prins and Prins cyclization of aryl epoxides: a facile synthesis of diaza-, oxa-aza-, and dioxa-bicycles

J Org Chem. 2010 Mar 19;75(6):2081-4. doi: 10.1021/jo902683p.

Authors

Jillu S Yadav¹, Prashant Borkar, P Pawan Chakravarthy, Basi V Subba Reddy, Akella V S Sarma, Shaik Jeelani Basha, Balasubramanian Sridhar, René Grée

Affiliation

¹ Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India. [email protected]

PMID: 20192165
DOI: 10.1021/jo902683p

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.