The proposed research should provide a better understanding of the stereochemical requirements of drugs interacting with adrenergic, dopaminergic and histaminergic receptors. The synthesis of optically active analogs of oxymetazoline, tolazoline, clonidine, tetrahydrozoline and 2-(3,4a-trihydroxybenzyl)-imidazoline is proposed in which the asymmetric center is at one of three positions in the molecule.