Enantioselective dihydroxylation of styrene (I) using AD-mix-alpha gave the (S)-diol (II). Tosylation of the primary hydroxyl group of (II), followed by nucleophilic displacement of the tosylate (III) with NaN3, provided azido alcohol (IV). The azido group of (IV) was then reduced to the corresponding amine (V) by catalytic hydrogenation in the presence of Pd/C. Finally, condensation of the chiral amino alcohol (V) with 1-methyl-5-cyanoindole (VI) in a hot mixture of ethylene glycol and glycerol yielded the target diaryl oxazolidine.