Subba Reddy, B. V. ; Borkar, Prashant ; Pawan Chakravarthy, P. ; Yadav, J. S. ; Gree, Rene (2010) Sc(OTf)3-catalyzed intramolecular aza-Prins cyclization for the synthesis of heterobicycles Tetrahedron Letters, 51 (26). pp. 3412-3416. ISSN 0040-4039
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Official URL: http://www.sciencedirect.com/science/article/pii/S...
Related URL: http://dx.doi.org/10.1016/j.tetlet.2010.04.093
Abstract
The coupling of (E)- and (Z)-hex-3-ene-1,6-ditosylamide with various aldehydes in the presence of 10 mol % Sc(OTf)3 gave the corresponding trans- and cis-fused 1,5-ditosyl-octahydro-1H-pyrrolo[3,2-c]pyridines, respectively, in good yields via intramolecular aza-Prins cyclization, whereas the coupling of (E)- and (Z)-N-(6-hydroxyhex-3-enyl)-4-methylbenzenesulfonamide afforded the corresponding trans- and cis-fused octahydro-1-tosylpyrano[4,3-b]pyrroles derivatives, respectively, via intramolecular Prins-cyclization.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | Lewis Acids; Intramolecular Aza-Prins Cyclization; Homoallyl Amide; Heterobicycles |
| ID Code: | 58747 |
| Deposited On: | 02 Sep 2011 03:41 |
| Last Modified: | 02 Sep 2011 03:41 |
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