Subba Reddy, B. V. ; Venkateswarlu, A. ; Borkar, Prashant ; Yadav, J. S. ; Kanakaraju, M. ; Kunwar, A. C. ; Sridhar, B. (2013) Thia-Prins Bicyclization Approach for the Stereoselective Synthesis of Dithia- and Azathia-Bicycles Journal of Organic Chemistry, 78 (12). pp. 6303-6308. ISSN 0022-3263
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Official URL: http://doi.org/10.1021/jo400680w
Related URL: http://dx.doi.org/10.1021/jo400680w
Abstract
A novel thia-Prins bicyclization approach has been developed for the first time for the synthesis of hexahydro-2H-thieno[3,2-c]thiopyran derivatives from the coupling of homoallylic mercaptans such as hex-3-ene-1,6-dithiol with various aldehydes using 10 mol % InBr3 in dichloromethane with high selectivity. In addition, the coupling of (E)-N-(6-mercaptohex-3-enyl)-4-methylbenzenesulfonamide with aldedydes affords the corresponding N-tosyloctahydrothiopyrano[4,3-b]pyrrole derivatives in good yields. This reaction is a stereoselective affording trans-fused product from E-homoallyllic mercaptan and cis-fused product from Z-homoallyllic mercaptan.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 135733 |
| Deposited On: | 11 Aug 2023 08:52 |
| Last Modified: | 11 Aug 2023 08:52 |
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