偕双硅2,3-环氧醇区域及立体选择性环氧开环/卤代反应研究

摘要

C3-位偕双硅取代的2,3-环氧醇分别与对甲苯磺酰氯、溴素和单质碘发生C3-位区域及立体选择性环氧开环/卤代反应合成了15个新的C3-位卤代偕双硅基1,2-二醇类产物,收率64%~87%,其结构经1H NMR, 13C NMR和HR-MS(ESI)表征.产物的立体结构经3-[二甲基(苯基)甲硅烷基]-3-碘-3-(三甲基甲硅烷基)丁烷-1,2-二醇(8d)的X-射线单晶衍射确证.%The reaction of C3-geminal bis(silane) substituted 2,3-epoxy alcohols with TsCl, Br2 and I2 proceeds by a regio-and diastereoselective C3-expoxide opening/halogenation process, giving 15 novel C3-halogenerated products in 64%~87% yields.The structures were characterized by 1H NMR, 13C NMR and HR-MS(ESI).The stereochemistry was confirmed by X-ray single crystal diffraction of 3-(dimethyl(phenyl)silyl)-3-iodo-3-(trimethylsilyl)butane-1,2-diol(8d).