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

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. H 2 O 2 has been developed. A mechanism for the asymmetric induction based...

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Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (6), p.123-1233
Main Authors: Dro d, Agnieszka, Chrobok, Anna
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Summary: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. H 2 O 2 has been developed. A mechanism for the asymmetric induction based on kinetic resolution of racemic carboxylic acids is proposed. A new method for the asymmetric chemo-enzymatic Baeyer-Villiger oxidation of 4-methylcyclohexanone to enantioenriched lactone in the presence of (±)-4-methyloctanoic acid, Candida Antarctica lipase B and 30% aq. H 2 O 2 has been developed.
ISSN:1359-7345
1364-548X
DOI:10.1039/c5cc08519e