Practical and convenient synthesis of N-heterocycles: stereoselective cyclization of N-alkenylamides with t-BuOI under neutral conditions.
Practical and convenient synthesis of N-heterocycles: stereoselective cyclization of N-alkenylamides with t-BuOI under neutral conditions.
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DOI：
10.1021/ol061182q
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发表时间：
2006-06
期刊：
影响因子：
5.2
通讯作者：
S. Minakata;Yoshinobu Morino;Yoji Oderaotoshi;M. Komatsu
中科院分区：
文献类型：
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作者：
S. Minakata;Yoshinobu Morino;Yoji Oderaotoshi;M. Komatsu
叔丁基次碘酸酯（t-BuOI）被发现是n -烯基酰胺环化的有力试剂，在极其温和的条件下产生各种n -杂环。当n -烯基磺酰胺参与反应时，三至六元饱和n -杂环具有良好的收率和完全的立体选择性。该方法适用于烯基苯酰胺衍生物的环化，得到N-、O-或N-、s -杂环。
[Structure: see text] tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cyclization of N-alkenylamides leading to a variety of N-heterocycles under extremely mild conditions. When N-alkenylsulfonamides were employed in the reaction, three- to six-membered saturated N-heterocycles were obtained in good to excellent yields with complete stereoselectivity. The method was applicable to the cyclization of alkenylbenzamide derivatives to afford N-, O- or N-, S-heterocycles.