We report here a rapid, efficient, and easy to handle process to access a variety of enantioenriched α‐gem‐difluorinated alcohols. A Rh(III)‐catalyzed asymmetric transfer hydrogenation method was developed in yields up to 98% and enantiomeric excesses up to >99%. The reduction proceeds under mild conditions with a range of difluorinated molecules including 3,3‐difluorochromanone, 3,3‐difluorothiochromanone, 3,3‐difluoro‐dihydroquinolinone and α‐difluorinated β‐ketosulfone derivatives to efficiently provide the desired enantioenriched difluorinated alcohols which are valuable novel fluorinated building blocks.