4.7 Article

Chiral Phosphoric Acid-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Naphthols with Isatin-Derived Ketimines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume -, Issue -, Pages -

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01659

Keywords

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Funding

  1. National Natural Science Foundation of China
  2. Applied Basic Research Project of Yunnan Province
  3. Department of Education of Yunnan Province
  4. Yunnan Provincial Key Laboratory Construction Plan Funding of Universities
  5. [21961045]
  6. [21572198]
  7. [2017FA004]
  8. [2018FB021]
  9. [2019Y0198]

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A wide range of chiral 3-amino-2-oxindoles were successfully synthesized with high optical purities through the enantioselective Friedel-Crafts addition of naphthols with isatin-derived ketimines using H8-BINOL-derived chiral biaryl phosphoric acid as the catalyst.
The enantioselective Friedel-Crafts addition of naphthols with isatin-derived ketimines was developed with H8- BINOL-derived chiral biaryl phosphoric acid. A wide range of isatin-derived ketimines and naphthols were successfully applied and gave a series of chiral 3-amino-2-oxindoles in excellent yields with high optical purities.

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