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Chinese Journal of Organic Chemistry >

2021 , Vol. 41 >Issue 10: 4039 - 4049

DOI: https://doi.org/10.6023/cjoc202105055

ARTICLES

Optically Active 3,4-Dihydrocoumarins via Organocatalyzed Asymmetric [4+2] Annulation of ortho-Hydroxyl Functionalized p-Quinone Methides with β-Keto Acylpyrazoles

  • Min Zhao ,
  • Fei Li ,
  • Yizheng Cheng ,
  • Youming Wang ,
  • Zhenghong Zhou
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  • a Institute and State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071
    b Department of Chemistry, College of Chemistry, Nankai University, Tianjin 300071
* Corresponding author. E-mail:

Received date: 2021-05-31

  Revised date: 2021-06-22

  Online published: 2021-07-05

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Abstract

An organocatalyzed asymmetric formal [4+2] annulation of ortho-hydroxyl functionalized p-quinone methides with β-keto acylpyrazoles has been developed, which provides an efficient approach to access optically active 3,4-dihydro- coumarins. Under the catalysis of a quinine-derived bifunctional squramide, the reactions of a wide range of ortho-hydroxy- phenyl substituted p-quinone methides and β-keto acylpyrazoles took place smoothly to generate the corresponding polysubstituted 3,4-dihydrocoumarins in good yields with high levels of diastereo- and enantio-selectivities (up to 96% yield, >19/1 dr and 98% ee) under mild reaction conditions.

Key words： asymmetric synthesis; 3,4-dihydrocoumarin; ortho-hydroxyphenyl-substituted para-quinone methide; β-keto acylpyrazole; organocatalysis

Cite this article

Min Zhao , Fei Li , Yizheng Cheng , Youming Wang , Zhenghong Zhou . Optically Active 3,4-Dihydrocoumarins via Organocatalyzed Asymmetric [4+2] Annulation of ortho-Hydroxyl Functionalized p-Quinone Methides with β-Keto Acylpyrazoles[J]. Chinese Journal of Organic Chemistry, 2021 , 41(10) : 4039 -4049 . DOI: 10.6023/cjoc202105055

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CCDC-2086168 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
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