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Oxidative Alkene Cleavage by Chemical and Enzymatic Methods
Author(s) -
Rajagopalan Aashrita,
Lara Miguel,
Kroutil Wolfgang
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300882
Subject(s) - alkene , chemistry , singlet oxygen , cleavage (geology) , ozonolysis , hypervalent molecule , molecule , combinatorial chemistry , ene reaction , photochemistry , organic chemistry , oxygen , catalysis , reagent , geotechnical engineering , fracture (geology) , engineering
The cleavage of alkenes to the corresponding carbonyl products is a widely employed method in organic synthesis, especially to introduce oxygen functionalities into molecules, remove protecting groups and tailor large molecules. Chemical methods available for alkene cleavage include, for instance, ozonolysis, several metal‐based variants (KMnO 4 , OsO 4 , RuO 4 , etc.), electrochemical alternatives, singlet oxygen, hypervalent iodine and organic molecules in combination with oxygen. Furthermore, several enzymatic methods for alkene cleavage have been described to establish safe, mild and selective oxidation methods. Various heme and non‐heme iron‐dependent enzymes catalyse the alkene cleavage at ambient temperature and atmospheric pressure in an aqueous buffer, showing good chemo‐ and regioselectivities in selected cases. Quite recently some Cu‐, Mn‐ and Ni‐dependent enzymes have been identified for this reaction. This review gives an overview of the different chemical and enzymatic methods available for the cleavage of alkenes.