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Third-party-funded project

Title:
Preparative Application of Peroxidic Oxidants for Oxygen-Transfer Reactions

Project management at the University of Würzburg:

• Prof. Dr. Dr. h.c. Waldemar Adam ,Tel: + 49 (0)931 8885334,Fax: + 49 (0)931 8884756,Mail: adam@chemie.uni-wuerzburg.de

Participating scientists:

• Dipl.-Chem. Sara Bosio
• Dipl.-Chem. Hans-Georg Degen
• Dr. Aurelia Pastor
• Dr. Chantu Saha-Möller ,Tel: + 49 (0)931 8884752,Fax: + 49 (0)931 8884756,Mail: sahamoel@chemie.uni-wuerzburg.de
• Dipl.-Chem. Simon Schambony
• Dipl.-Chem. Thomas Wirth
• Dipl.-Chem. Cong-Gui Zhao

Abstract:
In this project, we have explored chemo-, regio-, diastereo-, and enantioselective oxyfunctionalizations of organic substrates by peroxidic oxidants such as dioxiranes and perhydrates as well as singlet oxygen. The mechanisms of oxygen-transfer processes have been elucidated. The application of novel organic peroxides in synthetic chemistry is one of the major tasks of this project.

Key words:
    Singlet Oxygen
    Peroxide
    Dioxirane
    Allylic Hydroperoxide
    Dioxetane
    Endoperoxide
    Ene Reaction
    Asymmetric Oxidation
    Epoxidation
    CH Oxidation
    Heteroatom Oxidation

Projekt period: from 02.1998 to 12.2000

Funding institution:
DFG ,Granting date: 04.12.1997

Preceding project:
DFG AD 60/20-2

Publications:

• Adam, W.; Degen, H.-G.; Pastor, A.; Saha-Möller, C. R.; Schambony, S. B.; Zhao, C.-G.. (2000). Preparative Use of Peroxidic Oxidants for Oxygen-Transfer Reactions. Wiley-VCH. (monograph)
• Adam, W.; Bosio, S.; Turro, N. J.. (2002). Highly Diasteoselective Dioxetane Formation in the Photooxygenation of Enecarbamates with an Oxazolidinone Chiral Auxiliary: Steric Control in the [2+2] Cycloaddition of Singlet Oxygen through Conformational Alignment. J. Am. Chem.Soc., 124, 8814 -8815, (scientific article)
• Adam, W.; Saha-Möller, C. R.; Ganeshpure, P. A.. (2001). Synthetic Applications of Nonmetal Catalysts for Homogeneous Oxidation. Chem. Rev., 101, 3499 - 3548, (scientific article)
• Adam, W.; Saha-Möller, C. R.; Zhao, C.-G.. (1999). Asymmetric C-H Oxidation of vic Diol to α-Hydroxy Ketones by a Fructose-Derived Dioxetane: Electronic Effects on the Enantioselectivity of Oxygen Transfer. J. Org. Chem., 64, 7492 - 7497, (scientific article)
• Adam, W.; Saha-Möller, C. R.; Schambony, S. B.. (1999). A Highly Diastereoselective Dioxetane Formation by the Hydroxy-Directed [2+2] Cycloaddition of Singlet Oxygen to a Chiral Allylic Alcohol. J. Am. Chem. Soc., 121, 1834 - 1838, (scientific article)
• Adam, W.; Güthlein, M. ; Peters, E:-M.; Peters, K.; Wirth, T.. (1998). Chiral-Auxiliary-Induced Diasteroselectivity in the [4+2] Cycloadditions of Optically Active 2,2-Dimethyloxazolidine Derivatives of Sorbic Acid: A Model Study with Singlet Oxygen as the Smallest Dienophile. J. Am. Chem. Soc., 120, 4091 - 4093, (scientific article)

Links:
Additional Publications