Enantioselective Synthesis of 4-Hydroxy-3-(3-Oxo-1-Phenyl Butyl)- 2H-1-Benzopyran-2-One (Warfarin)

Authors: Ayhan S. DEMİR, Cihangir TANYELi, Volkan GÜLBEYAZ, Hülya AKGÜN

Abstract: Oral anticoagulant Warfarin (4-hydroxy-3-(3-oxo-1-phenyl butyl)-2H-1- benzopyran-2-one) is synthesized in optically active form starting from 4- hydroxycoumarin via formation of optically active enamines followed by Michael addition reaction with benzyliden acetone at low temperature. Different amines gave 17-68\% ee and the chemical yield was 22-71\%, depending on the reaction conditions and the structure of chiral amines.


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