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Keywords:

  • asymmetric synthesis;
  • fluorination;
  • Mannich reaction;
  • organocatalysis;
  • quaternary stereocenters
Thumbnail image of graphical abstract

Fluorinated quaternary stereocenters: A novel bifunctional catalyst 1 derived from natural tryptophan promoted the Mannich reaction of α-fluoro-β-ketoesters to afford fluorinated chiral molecules containing vicinal quaternary and tertiary stereogenic centers with exceptional enantioselectivity. An unprecedented α-fluoro-β-lactam was also prepared by this method (see scheme; Boc=tert-butoxycarbonyl).