Yadav, Jillu S. ; Borkar, Prashant ; Pawan Chakravarthy, P. ; Subba Reddy, Basi V. ; Sarma, Akella V. S. ; Basha, Shaik Jeelani ; Sridhar, Balasubramanian ; Grée, René (2010) Versatile intramolecular aza-prins and Prins cyclization of aryl epoxides: a facile synthesis of diaza-, oxa-aza-, and dioxa-bicycles Journal of Organic Chemistry, 75 (6). pp. 2081-2084. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo902683p
Related URL: http://dx.doi.org/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°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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 63137 |
| Deposited On: | 28 Sep 2011 03:48 |
| Last Modified: | 28 Sep 2011 03:48 |
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