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Organocatalyzed Friedel–Craft-type reaction of 2-naphthol with β,γ-unsaturated α-keto ester to form novel optically active naphthopyran derivatives

Tetrahedron: Asymmetry, ISSN: 0957-4166, Vol: 19, Issue: 23, Page: 2699-2704
2008
  • 77
    Citations
  • 0
    Usage
  • 22
    Captures
  • 0
    Mentions
  • 0
    Social Media
Metric Options:   Counts1 Year3 Year

Metrics Details

  • Citations
    77
    • Citation Indexes
      77
  • Captures
    22

Article Description

A novel bifunctional thiourea–tertiary-amine-catalyzed enantioselective Friedel–Craft-type addition reaction of 2-naphthol with β,γ-unsaturated α-keto ester was developed. Subsequent dehydration of the reaction adducts with a catalytic amount of concentrated H 2 SO 4 in a one-pot fashion readily afforded a series of new optically active naphthopyran derivatives with moderate to good yields (up to 91%) and enantioselectivities (up to 90%).

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