Stereoselective synthesis of 3-methyleneisoindolin-1-ones via base-catalyzed intermolecular reactions of electron-deficient alkynes with N-hydroxyphthalimides.
Stereoselective synthesis of 3-methyleneisoindolin-1-ones via base-catalyzed intermolecular reactions of electron-deficient alkynes with N-hydroxyphthalimides.
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DOI：
10.1021/acs.joc.5b00002
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发表时间：
2015-03
期刊：
影响因子：
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通讯作者：
Xin Chen;Fei-fei Ge;T. Lu;Qing-Fa Zhou
中科院分区：
文献类型：
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作者：
Xin Chen;Fei-fei Ge;T. Lu;Qing-Fa Zhou
通过基础催化策略，开发了缺电子炔烃与 N-羟基邻苯二甲酰亚胺的高度立体选择性分子间反应，以有效构建 N-未保护的 3-亚甲基异吲哚啉-1-酮。炔酸酯与N-羟基邻苯二甲酰亚胺在Bu3P在DMF中于150℃下反应得到相应的具有(Z)构型的3-亚甲基异吲哚啉-1-酮，而炔酸酯与N-羟基邻苯二甲酰亚胺在K2CO3在DMF中在60℃下反应得到相应的3-亚甲基异吲哚啉-1-酮。当炔酮与N-羟基邻苯二甲酰亚胺反应时，得到(E)-构型和(Z)-3-亚甲基异吲哚啉-1-酮。
Highly stereoselective intermolecular reactions of electron-deficient alkynes with N-hydroxyphthalimides for efficient construction of N-unprotected 3-methyleneisoindolin-1-ones have been developed through base catalytic strategies. The reaction of alkynoates with N-hydroxyphthalimides catalyzed by Bu3P in DMF at 150 °C gave the corresponding 3-methyleneisoindolin-1-ones with a (Z)-configuration, while the reaction of alkynoates with N-hydroxyphthalimides catalyzed by K2CO3 in DMF at 60 °C gave the corresponding 3-methyleneisoindolin-1-ones with an (E)-configuration, and (Z)-3-methyleneisoindolin-1-ones were obtained when alkyne ketones reacted with N-hydroxyphthalimide.