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

• Published in: Journal of organic chemistry Vol. 75; no. 6; pp. 2081 - 2084
• Main Authors: Yadav, Jillu S, Borkar, Prashant, Chakravarthy, P. Pawan, Subba Reddy, Basi V, Sarma, Akella V. S, Basha, Shaik Jeelani, Sridhar, Balasubramanian, Grée, René
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 19-03-2010
• Subjects: Chemical Sciences; Chemistry; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings; Organic chemistry; Preparations and properties; Intramolecular reaction; Pyridine; Nitrogen heterocycle; Epoxide; Bicyclic compound; Aromatic compound; Selectivity; Oxygen heterocycle; Chemical synthesis; Prins reaction; Ethylenic compound
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo902683p

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 °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.