A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopenteneand cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 degrees C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 degrees C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.

Biocatalytic synthesis of chiral cyclic gamma-oxoesters by sequential C-H hydroxylation, alcohol oxidation and alkene reduction

Elisabetta Brenna;Michele Crotti;Francesco G. Gatti;Fabio Parmeggiani;Andrea Pugliese;TENTORI, FRANCESCA
2017-01-01

Abstract

A three-step biocatalytic procedure is described for the conversion of methyl and ethyl cyclopenteneand cyclohexenecarboxylates into both the enantiomers of the corresponding chiral 3-oxoesters, which are useful building blocks for the synthesis of active pharmaceutical ingredients. The allylic hydroxylation of the starting cycloalkenecarboxylates is carried out by using R. oryzae resting cells entrapped in alginate beads, in acetate buffer solution at 25 degrees C. The oxidation of the intermediate allylic alcohols to unsaturated ketones, performed by the laccase/TEMPO system, and the ene-reductase mediated hydrogenation of the alkene bond were carried out in the same reaction vessel in a sequential mode at 30 degrees C. Being entirely biocatalytic, our multistep procedure provides considerable advantages in terms of selectivity and environmental impact over reported chemical methods.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/1044785
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