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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 6: 1722 - 1734

DOI: https://doi.org/10.6023/cjoc202112023

ARTICLES

Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles

  • Xing Wang ,
  • Qianqian Song ,
  • Xuling Chen ,
  • Pengfei Li ,
  • Yunkun Qi ,
  • Wenjun Li
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  • a School of Pharmacy, Qingdao University, Qingdao, Shandong 266073
    b Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, South University of Science and Technology of China, Shenzhen, Guangzhou 518055
† These authors contributed equally to this work
*E-mail: ;
;

Received date: 2021-12-18

  Revised date: 2022-02-28

  Online published: 2022-03-08

Supported by

Natural Science Foundation of Shandong Province(ZR2021MB026); Special Funds of the Taishan Scholar Program of Shandong Province(tsqn201812047); Shenzhen Innovation of Science and Technology Commission(20200925151614002); Guangdong Provincial Key Laboratory of Catalysis(2020B121201002)

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Abstract

A chiral phosphoric acid catalyzed aza-1,8-conjugate addition of isoxazol-5(4H)-ones to 6-methylene-6H-indoles formed in situ from 6-indolylmethanols has been developed for the first time. Notably, the remote stereocontrolled 1,8-addition of isoxazol-5(4H)-ones was featured by N-selectivity, affording aza-adducts in 70%~83% yields with 61%~96% ee.

Key words： asymmetric organocatalysis; conjugate addition; isoxazol-5(4H)-ones; 6-methylene-6H-indole

Cite this article

Xing Wang , Qianqian Song , Xuling Chen , Pengfei Li , Yunkun Qi , Wenjun Li . Organocatalytic Regio- and Enantioselective aza-1,8-Conjugate Additions of Isoxazol-5(4H)-ones to 6-Methide-6H-indoles[J]. Chinese Journal of Organic Chemistry, 2022 , 42(6) : 1722 -1734 . DOI: 10.6023/cjoc202112023

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