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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 1: 348 - 356

DOI: https://doi.org/10.6023/cjoc202006036

Article

Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes

  • Huiling Wen ,
  • Nianhua Luo ,
  • Lu Ouyang ,
  • Renshi Luo
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  • a School of Pharmacy, Gannan Medical University, Ganzhou, Jiangxi 341000

Received date: 2020-06-19

  Revised date: 2020-08-09

  Online published: 2020-08-27

Supported by

the National Natural Science Foundation of China(21962004); the National Natural Science Foundation of China(21562004); the Jiangxi Provincial Department of Science and Technology(20192BAB203004); the Foundation of Jiangxi Provincial Department of Education(GJJ190829); Gannan Medical University(QD201832); Gannan Medical University(QD201816); Gannan Medical University(YJ202027)

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Abstract

A highly enantioselective [3+3] aza-cyclization of α, β-unsaturated aldehydes with 3-aminobenzofuran promoted by diphenylperhydroindolinol silyl ether has been described, which afforded benzofuran derivatives in high yields (up to 93%), diastereoselectivities ( dr>20∶1) and enantioselectivities (86%~>99% ee). This method also enabled to obtain benzofuran derivatives in gram scale-up.

Key words： diphenylperhydroindolinol silyl ether; [3+3] aza-cyclizationαβ-unsaturated aldehydes; 3-aminobenzofuran

Cite this article

Huiling Wen , Nianhua Luo , Lu Ouyang , Renshi Luo . Synthesis of Benzofuran Derivatives by Diphenylperhydroindolinol Silyl Ether-Catalyzed Asymmetric [3+3] Aza-cyclization ofα,β-Unsaturated Aldehydes[J]. Chinese Journal of Organic Chemistry, 2021 , 41(1) : 348 -356 . DOI: 10.6023/cjoc202006036

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