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Citation: Tian Zaiwen, Fu Zhitao, Zhang Wanxuan, Ren Jun. Synthesis of Highly Substituted Pyrrolo[1, 2-a]indoles Catalyzed by Chiral Phosphoric Acid[J]. Chinese Journal of Organic Chemistry, ;2016, 36(9): 2212-2215. doi: 10.6023/cjoc201602036 shu

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

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

Corresponding author: Zhang Wanxuan, zhangwx@hubu.edu.cn Ren Jun,
Received Date: 29 February 2016
Revised Date: 21 May 2016

Fund Project: by the Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education, Hubei University 2013-KL-009

Figures(2)

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).
- cycloaddition,
- organocatalysis,
- heterocycles,
- enantioselectivity
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