Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 4039-4049.DOI: 10.6023/cjoc202105055 Previous Articles     Next Articles

ARTICLES

有机催化邻羟基官能化的对甲亚基苯醌和β-氧代酰基吡唑的不对称[4+2]环化合成光学活性3,4-二氢香豆素衍生物

赵敏a, 李霏a, 程益政b, 王有名a, 周正洪a,*()   

  1. a 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
    b 南开大学化学学院化学系 天津 300071
  • 收稿日期:2021-05-31 修回日期:2021-06-22 发布日期:2021-07-05
  • 通讯作者: 周正洪

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

Min Zhaoa, Fei Lia, Yizheng Chengb, Youming Wanga, Zhenghong Zhoua()   

  1. 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
  • Received:2021-05-31 Revised:2021-06-22 Published:2021-07-05
  • Contact: Zhenghong Zhou

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