The synthesis of four novel analogues of metoprolol, a well-known β1-blocker used to reduce arterial blood pressure, is described. The preparation of (2S, 2′ S)-7,(2R, 2′ S)- 7,(2R, 2′ R)-8, and (2S, 2′ R)-8 was based on the reaction of racemic 2-[4-(2′- methoxyethyl)-phenoxymethyl]-oxirane (4) with (R)-or (S)-2-amino-1-butanol. Salient characteristics of analogues 7 and 8 relative to metoprolol are the incorporation of an ...