Chemo-enzymatic Baeyer–Villiger oxidation of 4-methylcyclohexanone via kinetic resolution of racemic carboxylic acids: direct access to enantioenriched lactone

Abstract

A new method for the asymmetric chemo-enzymatic Baeyer–Villiger oxidation of prochiral 4-methylcyclohexanone to (R)-4-methylcaprolactone in the presence of (±)-4-methyloctanoic acid, Candida Antarctica lipase B and 30% aq. H₂O₂ has been developed. A mechanism for the asymmetric induction based on kinetic resolution of racemic carboxylic acids is proposed.