Chemoselective addition of (difluoromethyl)trimethylsilane (CHF2SiMe3) to the carbonyl bond of aryl glyoxal derived α-imino ketones, and selected diaryl 1,2-diketones were studied in the presence of initiators, such as potassium tert-butoxide or caesium fluoride. Subsequent reduction of the obtained α-imino alcohols and α-hydroxy ketones with sodium borohydride gave the expected 2-amino 1-(difluoromethyl)alcohols and (difluoromethyl)-1,2-diols respectively in moderate to good yields. High de values were observed for the reduction of α-(difluoromethyl)-α-hydroxy ketones.