title: 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.
authors.affiliation: Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India. yadavpub@iict.res.in
authors.forename: Jillu S
authors.initials: JS
authors.lastname: Yadav
authors.forename: Prashant
authors.initials: P
authors.lastname: Borkar
authors.forename: P Pawan
authors.initials: PP
authors.lastname: Chakravarthy
authors.forename: Basi V Subba
authors.initials: BV
authors.lastname: Reddy
authors.forename: Akella V S
authors.initials: AV
authors.lastname: Sarma
authors.forename: Shaik Jeelani
authors.initials: SJ
authors.lastname: Basha
authors.forename: Balasubramanian
authors.initials: B
authors.lastname: Sridhar
authors.forename: René
authors.initials: R
authors.lastname: Grée