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2016 , Vol. 36 >Issue 9: 2212 - 2215

DOI: https://doi.org/10.6023/cjoc201602036

研究简报

手性磷酸催化合成多取代吡咯并[1,2-a]吲哚

  • 田再文 ,
  • 付直涛 ,
  • 张万轩 ,
  • 任君
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  • 湖北大学有机化工新材料湖北省协同创新中心 有机功能分子合成与应用教育部重点实验室 武汉 430062

收稿日期: 2016-02-29

  修回日期: 2016-05-21

  网络出版日期: 2016-06-01

基金资助

湖北大学有机功能分子合成与应用教育部重点实验室（No.2013-KL-009）资助项目.

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Synthesis of Highly Substituted Pyrrolo[1,2-a]indoles Catalyzed by Chiral Phosphoric Acid

  • Tian Zaiwen ,
  • Fu Zhitao ,
  • Zhang Wanxuan ,
  • Ren Jun
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  • Hubei Collaborative Innovation Center for Advanced Organic Chemical Material, Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University, Wuhan 430062

Received date: 2016-02-29

  Revised date: 2016-05-21

  Online published: 2016-06-01

Supported by

Project supported by the Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University (No.2013-KL-009).

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摘要

以联萘二酚骨架的手性磷酸催化吲哚苄基醇和3-吲哚丙烯酸酯发生环加成反应，产生三个连续的手性中心.当使用3，3'-位被α-萘取代的联萘二酚骨架手性磷酸为催化剂时，反应的效果最佳，产率最高达91%以上，非对映选择性为9∶1~20∶1，对映选择性为62%~92%.

关键词： 环加成; 有机催化; 杂环; 对映选择性

本文引用格式

田再文 , 付直涛 , 张万轩 , 任君 . 手性磷酸催化合成多取代吡咯并[1,2-a]吲哚[J]. 有机化学, 2016 , 36(9) : 2212 -2215 . DOI: 10.6023/cjoc201602036

Abstract

The cycloaddition reaction of a suitably substituted indolyl benzylic alcohol with an ethyl 3-indoleacrylate catalyzed by phos-phoric acids derived from (S)-BINOL was described. When the chiral phosphoric acid bearing α-naphthyl at 3,3'-positions of the binaphthyl was used as a catalyst, pyrrolo[1,2-a]indole derivatives with three contiguous stereocenters were obtained in high yield up to 91%, with good to high diastereoselectivity (9/1~20/1 dr) and enantioselectivity (62%~92% ee for the major dia-stereoisomer).

Key words： cycloaddition; organocatalysis; heterocycles; enantioselectivity

参考文献

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