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首页> 外文期刊>Chemistry: A European journal >Stereoselective [3+2] Carbocyclization of Indole-Derived Imines and Electron-Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives
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Stereoselective [3+2] Carbocyclization of Indole-Derived Imines and Electron-Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives

机译：吲哚衍生的亚胺和富含电子的烯烃的立体选择性[3 + 2]碳环化：环戊[b]吲哚或四氢喹啉衍生物的不同合成

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摘要

An unprecedented stereoselective [3+2] carbocyclization reaction of indole-2-carboxaldehydes, anilines, and electron-rich alkenes to obtain cyclopenta[b]indoles is disclosed. This pathway is different from the well-established Povarov reaction: the formal [4+2] cycloaddition involving the same components, which affords tetrahydroquinolines. Moreover, by simply changing the Bronsted acid catalyst, this multicomponent coupling process could be divergently directed towards the conventional Povarov pathway to produce tetrahydroquinolines or to the new pathway (anti-Povarov) to generate cyclopenta[b] indoles. Supported by computational studies, a stepwise Mannich/Friedel-Crafts cascade is proposed for the new anti-Povarov reaction, whereas a concerted [4+2] cycloaddition mechanism is proposed for the Povarov reaction.
机译：公开了前所未有的吲哚-2-羧醛，苯胺和富含电子的烯烃的立体选择[3 + 2]碳环化反应，以获得环戊[b]吲哚。该途径与公认的Povarov反应不同：涉及相同成分的正式[4 + 2]环加成反应产生四氢喹啉。而且，通过简单地改变布朗斯台德酸催化剂，该多组分偶联过程可以发散地指向常规的Povarov途径以产生四氢喹啉或指向新的途径（抗Povarov）以产生环戊[b]吲哚。在计算研究的支持下，提出了逐步的Mannich / Friedel-Crafts级联用于新的抗Povarov反应，而提出了协同的[4 + 2]环加成机理用于Povarov反应。

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