Dong Jun, Xu Jiaxi
State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.
Org Biomol Chem. 2017 Jan 25;15(4):836-844. doi: 10.1039/c6ob02387h.
Thietanes are pharmaceutically important cores of some biological compounds and intermediates of organic synthesis. Various thietanes were prepared from thiiranes via ring expansion through a reaction with trimethyloxosulfonium iodide in the presence of sodium hydride. The reaction process is a nucleophilic ring-opening reaction of thiiranes with dimethyloxosulfonium methylide, generated from trimethyloxosulfonium iodide and sodium hydride, and subsequent intramolecular displacement (cyclization) of thiolates to the dimethyloxosulfonium moiety. The current method provides a new strategy for efficient preparation of thietanes from readily available thiiranes.
噻丁环是一些生物化合物的重要药用核心以及有机合成的中间体。通过在氢化钠存在下与三甲基氧化锍碘化物反应，经由扩环反应从硫杂环丙烷制备了各种噻丁环。该反应过程是硫杂环丙烷与由三甲基氧化锍碘化物和氢化钠生成的二甲基氧化锍甲基叶立德的亲核开环反应，以及随后硫醇盐向二甲基氧化锍部分的分子内取代（环化）反应。目前的方法为从容易获得的硫杂环丙烷高效制备噻丁环提供了一种新策略。
