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

Autor:	Bernardin, Akagah, François, Estour, Philippe, Vérité, Pédro, Lameiras, Mohammed, Nour, Christian, Cavé, Sabine, Ménager, Olivier, Lafont
Rok vydání:	2004
Předmět:	Magnetic Resonance Spectroscopy Porphyrins Formates Molecular Structure Metalloporphyrins Temperature Stereoisomerism Naphthalenes Catalysis Oxygen Models Chemical Biomimetics Steroids Oxidation-Reduction
Zdroj:	Chirality. 16(6)
ISSN:	0899-0042
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=pmid________::126cb9d6d69e35457752bd350d9baf8f https://pubmed.ncbi.nlm.nih.gov/15190585 Zobrazit plný text záznamu Plný text