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Asymmetric synthesis of tranylcypromine was achieved using an enantioselective SimmonsSmith cyclopropanation catalyzed by a simple disulfonamide derived from an α-amino acid. The optically active milnacipran was also synthesized by porcine pancreas lipase-catalyzed selective monoacylation of the C4-hydroxy group in (Z)-2-phenylbut-2-ene-1,4-diol and the enantioselective Simmons-Smith cyclopropanation as the key steps. [ABSTRACT FROM AUTHOR]