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Keywords:

  • enantioselectivity;
  • fluoroalkylation;
  • pyrrolidines;
  • radical reactions;
  • synthetic methods
Thumbnail image of graphical abstract

A radical synthon: Nucleophilic (phenylthio)difluoromethylation of (R)-N-(tert-butylsulfinyl)imines with 1, a difluoromethylene radical anion equivalent, afforded the corresponding products in good yields and with high diastereoselectivity (d.r.≥98:2). The resulting PhSCF2-containing sulfinamides can be further transformed into chiral 2,4-trans-disubstituted 3,3-difluoropyrrolidines through an intramolecular radical cyclization methodology.