Abstract The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysts that are readily accessible from (1S, 2R)-ephedrine and (1R, 2S)-ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.