Premium
Regio‐ and diastereocontrolled preparative oxidation of methyloctalones by a biomimetic porphyrin catalyst
Author(s) -
Akagah Bernardin,
Estour François,
Vérité Philippe,
Lameiras Pédro,
Nour Mohammed,
Cavé Christian,
Ménager Sabine,
Lafont Olivier
Publication year - 2004
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20043
Subject(s) - chemistry , porphyrin , diastereomer , synthon , hydroxylation , imidazole , chirality (physics) , catalysis , enantiomer , allylic rearrangement , stereochemistry , ring (chemistry) , biomimetic synthesis , combinatorial chemistry , organic chemistry , enzyme , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
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. Chirality 16:398–403, 2004. © 2004 Wiley‐Liss, Inc.