Chemistry Letters, Vol.42, No.10, 1311-1313, 2013
Asymmetric Syntheses of Pharmaceuticals Containing a Cyclopropane Moiety Using Catalytic Asymmetric Simmons-Smith Reactions of Allylalcohols: Syntheses of Optically Active Tranylcypromine and Milnacipran
Asymmetric synthesis of tranylcypromine was achieved using an enantioselective Simmons-Smith cyclopropanation catalyzed by a simple disulfonamide derived from an alpha-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.