Synthesis of 5-Membered Sulfur Heterocycles via Tin-Catalyzed Annulation of Mercapto Ketones with Activated Alkenes
Synthesis of 5-Membered Sulfur Heterocycles via Tin-Catalyzed Annulation of Mercapto Ketones with Activated Alkenes
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锡催化巯基酮与活化烯烃成环合成五元硫杂环
DOI：
10.1021/acs.joc.9b03055
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Shibata Ikuya
中科院分区：
文献类型：
--
作者：
Suzuki Itaru;Sakamoto Yuki;Seo Yuta;Ninomaru Yoriko;Tokuda Kodai;Shibata Ikuya
以Sn（Oct）2- 2 MeOH为催化剂，将α-巯基酮1和活性烯2高效转化为S-杂环化合物。得到了二氢噻吩3和硫杂环戊烷4两种产物。产物的选择性取决于反应温度和加热条件下S-杂环从3到4的重排。将二氢噻吩3转化为有用的硫代内酯6 - 8和噻吩9。
Efficient conversion of α-mercapto ketones1with activated alkenes2into S-heterocycles was developed with Sn(Oct)2–2MeOH acting as a catalyst. Two types of products, dihydrothiophene3and thiolane4, were obtained. The selectivity of the products was dependent on the reaction temperature and on the rearrangement of the S-heterocycles from3to4under heating conditions. The dihydrothiophenes3were transformed into useful thiolactones6–8and thiophene9.