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
首次开发了一种新颖的thia-Prins双环化方法,用于通过均质
硫醇(如hex-3-ene-1,6)的偶合反应合成六氢-2 H-
噻吩并[3,2- c ]
硫代
吡喃衍
生物。在
二氯甲烷中使用10 mol%InBr 3具有高选择性的-二
硫醇与各种醛。另外,(E)-N-(6-巯基己基-3-烯基)-4-甲基苯磺酰胺与
醛类的偶联以良好的产率提供了相应的N-
甲苯磺酰基氢
硫代
吡喃并[4,3- b ]
吡咯衍
生物。这反应是立体选择性得到反式从-融合产品Ë -homoallyllic
硫醇和Z-均烯丙基
硫醇的顺式融合产物。