Regio- and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst - Normandie Université Access content directly
Journal Articles Chirality Year : 2004

Regio- and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst

Abstract

Both enantiomers of methyloctalone were oxidized by a biomimetic manganese/porphyrin/imidazole catalytic system in order to obtain sufficient amounts of various model metabolites. The double bond proved to be less sensitive than the ring methylenes. Hydroxylation occurred mainly in the allylic position (position 8) and also at positions 7 and 6. In position 8, two diastereomers were obtained while in positions 7 and 6 the reaction was diastereospecific. In the case of position 8 only the oxidation yielded a keto compound. The efficiency of this method for the preparation of functionalized chiral synthons was better than it was for biological pathways

Dates and versions

hal-02375819 , version 1 (22-11-2019)

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Bernardin Akagah, François Estour, Philippe Vérité, Pedro Lameiras, Mohammed Nour, et al.. Regio- and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst. Chirality, 2004, 16 (6), pp.398-403. ⟨10.1002/chir.20043⟩. ⟨hal-02375819⟩
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