Trifluoromethyl-stabilized optically active oxiranyl and aziridinyl anions for stereospecific syntheses of trifluoromethylated compounds

Optically active 2,3-epoxy-1,1,1-trifluoropropane was converted into the corresponding oxiranyl anion and reacted with electrophiles such as aldehydes, ketones and halides to give the corresponding adducts in moderate to good yields. The whole reaction occurred with retention of configuration at the stereogenic carbon center. In a similar manner, trifluoromethyl stabilizing aziridinyl anions were generated from the optically active N-tosyl and N-anisyl-2-trifluoromethylaziridines. They also reacted well with various electrophiles. The products of these reactions are versatile synthetic intermediates useful for the synthesis of a variety of trifluoromethylated compounds with quaternary chiral carbon centers.