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有机化学
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有机化学 ›› 2016, Vol. 36 ›› Issue (9): 2212-2215.DOI: 10.6023/cjoc201602036 上一篇    下一篇

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   

  1. 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 发布日期:2016-06-01
  • 通讯作者: 张万轩, 任君 E-mail:zhangwx@hubu.edu.cn
  • 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.

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

Tian Zaiwen, Fu Zhitao, Zhang Wanxuan, Ren Jun   

  1. 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:2016-02-29 Revised:2016-05-21 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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补充材料

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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

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