Kinetic resolution of heterocyclic amines by reaction with optically active acid chlorides.: The effect of reaction conditions on the diastereoselectivity of acylation of (±)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine

The influence of the reaction conditions (solvent, base) on the diastereoselectivity of acylation of (+/-)-3-methyl-2,3-dihydro-4H-1,4-benzoxazine with (S)-naproxen and N-tosyl(S)-proline chlorides was studied. The highest diastereoselectivity was observed for the reaction carried out in benzene in the presence of aliphatic tertiary amines.