Development of ruthenium catalyzed oxidation reactions inspired by cytochrome P-450

Abstract

Simulation of the functions of cytochrome P-450 with transition-metal catalysts such as ruthenium complex catalysts led to the discovery of biomimetic catalytic oxidation reactions of various substrates such as amines, amides, olefins, alcohols, phenols, ketones and hydrocarbons. These catalytic reactions are practical and highly useful for synthesis of biologically active compounds, which include cortisone acetate and adriamicine acetate. Importantly, (1R, 3S)-3-[1′-(t-butyldimethylsilyloxy) ethyl] azetidi-2-one can be converted to the corresponding 4-acetoxyazetidinone, which is a versatile and key intermediate for the synthesis of carbapenem antibiotics, with extremely high diastereoselectivify (99% yield, 99% de). This becomes important industrial process. The oxidations of amines and amides provide highly useful 4 methods for introduction of a substituent at the α-position of amines by the oxidation of amines and amides and subsequent treatment with nucleophiles.