4.6 Article

Squaramide-catalysed asymmetric Friedel-Crafts alkylation of naphthol and unsaturated pyrazolones†‡

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 19, Issue 15, Pages 3370-3373

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1ob00347j

Keywords

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Funding

  1. NSFC [81473100, 31900033]
  2. DIMP [2018ZX09711-001-001-017]
  3. Primary Research AMP
  4. Development Plan of Shanxi Province [201903D321110]
  5. Hospital Level Research Fund of Heping Hospital [HPYJ201927]

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The study achieved highly efficient asymmetric Michael-type Friedel-Crafts alkylation of naphthol and unsaturated pyrazolones under mild reaction conditions. A wide range of substrates were tolerated with excellent yields (up to 99%) and reasonable enantioselectivities (up to 96% ee) in the presence of the chiral squaramide catalyst.
The first method for highly efficient asymmetric Michael-type Friedel-Crafts alkylation of naphthol and unsaturated pyrazolones has been accomplished under mild reaction conditions. In the presence of the chiral squaramide catalyst, a wide range of substrates are tolerated in excellent yields (up to 99%) with reasonable enantioselectivities (up to 96% ee).

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