Development of Ruthenium Catalyzed Oxidation Reactions Inspired by Cytochrome P-450

• Murahashi Shun-Ichi

  Okayama University of Science, Department of Chemistry

Bibliographic Information

Other Title

• シトクロムP-450酵素を範とするルテニウム触媒を用いる酸化触媒反応の開拓

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.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 65 (1), 2-13, 2007

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• biomimetic oxidation
• cytochrome P-450
• ruthenium catalyst
• oxidation of amines
• synthesis of imines
• synthesis of nitrone
• oxidation of β-lactam
• α-ketol synthesis
• oxidation of phenol
• oxidation of hydrocarbon

Details

• CRID: 1390282680289544320
• NII Article ID: 10018461586
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.65.2
• ISSN: 18836526
• ISSN: 00379980
• Data Source:
  • JaLC
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed