Abstract

An efficient synthetic route to highly substituted pyrrolidone derivatives has been developed from an easily available alkynyl carboxamide and 4-methylbenzenesulfonic acid (PTSA). In the reaction, PTSA is not only used as acid catalyst but also as a reactant to provide a source for OTs group. A mechanism is proposed to involve the protonation of the alcohol substrate/cyclopropylcarbinol-homoallylic rearrangement/intramolecular N-nucleophilic cyclization reactions.

An efficient synthetic route to highly substituted pyrrolidone derivatives has been developed from an easily available alkynyl carboxamide and 4-methylbenzenesulfonic acid (PTSA). In the reaction, PTSA is not only used as acid catalyst but also as a reactant to provide a source for OTs group. A mechanism is proposed to involve the protonation of the alcohol substrate/cyclopropylcarbinol-homoallylic rearrangement/intramolecular N-nucleophilic cyclization reactions.

中文翻译：

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分子内环加成法从炔基羧酰胺和PTSA构建多取代的吡咯烷酮

摘要

从容易获得的炔基羧酰胺和4-甲基苯磺酸（PTSA）已经开发出一种高效合成高取代吡咯烷酮衍生物的途径。在该反应中，PTSA不仅用作酸催化剂，还用作提供OTs基团来源的反应物。提出了一种机制，涉及醇底物/环丙基甲醇-均烯丙基重排/分子内N-亲核环化反应的质子化。

从容易获得的炔基羧酰胺和4-甲基苯磺酸（PTSA）已经开发出一种高效合成高取代吡咯烷酮衍生物的途径。在该反应中，PTSA不仅用作酸催化剂，还用作提供OTs基团来源的反应物。提出了一种机制，涉及醇底物/环丙基甲醇-均烯丙基重排/分子内N-亲核环化反应的质子化。