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Thia-Prins Bicyclization Approach for the Stereoselective Synthesis of Dithia- and Azathia-Bicycles

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NIAID Data Ecosystem2026-03-07 收录
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https://figshare.com/articles/dataset/Thia_Prins_Bicyclization_Approach_for_the_Stereoselective_Synthesis_of_Dithia_and_Azathia_Bicycles/2403082
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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.
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2016-02-19
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