Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Development of Ruthenium Catalyzed Oxidation Reactions Inspired by Cytochrome P-450
Shun-Ichi Murahashi
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2007 Volume 65 Issue 1 Pages 2-13

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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 diastereoselectivity (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.
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© The Society of Syhthetic Organic Chemistry, Japan
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