芳基环氧化物的多功能分子内氮杂-Prins 和 Prins 环化反应：二氮杂、氧杂氮杂和二氧杂双环的简便合成方法。
Versatile intramolecular aza-Prins and Prins cyclization of aryl epoxides: a facile synthesis of diaza-, oxa-aza-, and dioxa-bicycles.
机构信息
Division of Organic Chemistry, Indian Institute of Chemical Technology, Hyderabad-500 007, India.
出版信息
J Org Chem. 2010 Mar 19;75(6):2081-4. doi: 10.1021/jo902683p.
Aryl epoxides undergo coupling smoothly with (E)-hex-3-ene-1,6-ditosylamide in the presence of 10 mol % p-TSA in 1,2-dichloroethane at 75 degrees C to produce the corresponding 1,5-ditosyl-octahydro-1H-pyrrolidino[3,2-c]pyridines in good yields with high trans-selectivity, whereas the coupling of (Z)-hex-3-ene-1,6-ditosylamide gave cis-fused octahydro-1H-pyrrolidino[3,2-c]pyridines predominantly. The use of readily available p-TSA makes this method simple, convenient, and practical.
芳基环氧化物在 1,2-二氯乙烷中，于 75°C、10mol%对甲苯磺酸（p-TSA）存在下，与顺式-己-3-烯-1,6-二对甲苯磺酰胺（E）-hex-3-ene-1,6-ditosylamide 平稳地耦合，以高产率和高反式选择性生成相应的 1,5-二对甲苯磺酰基-八氢-1H-吡咯并[3,2-c]吡啶；而（Z）-己-3-烯-1,6-二对甲苯磺酰胺的耦合主要得到顺式稠合的八氢-1H-吡咯并[3,2-c]吡啶。使用易得的对甲苯磺酸（p-TSA）使该方法简单、方便和实用。
Zotero 插件