The implementation of light-driven catalytic processes in biocatalysis opens a golden window of opportunities. We hereby report the merging of photocatalytic C−C bond formation with enzymatic asymmetric reduction for the direct conversion of simple aldehydes and acrylates or unsaturated carboxylic acids into chiral γ-lactones. Tetrabutylammonium decatungstate (TBADT) is employed as the photocatalyst to trigger the hydroacylation of the starting olefins, yielding the corresponding keto esters/acids. Subsequently, an alcohol dehydrogenase converts the intermediate to the chiral alcohol, which undergoes lactonization to the desired γ-lactone. The photochemoenzymatic synthesis of aliphatic and aromatic γ-lactones was thereby achieved with up to >99 % ee and >99 % yield. This synthesis highlights the power of building molecular complexity by merging photocatalysis with biocatalysis to access high-value added chiral compounds from simple, cheap and largely available starting materials.

The Synthesis of Chiral γ-Lactones by Merging Decatungstate Photocatalysis with Biocatalysis / Feyza Özgen, Fatma; Jorea, Alexandra; Capaldo, Luca; Kourist, Robert; Ravelli, Davide; Schmidt, Sandy. - In: CHEMCATCHEM. - ISSN 1867-3880. - 14:19(2022), pp. e202200855-e202200855. [10.1002/cctc.202200855]

The Synthesis of Chiral γ-Lactones by Merging Decatungstate Photocatalysis with Biocatalysis

Luca Capaldo;Davide Ravelli;
2022-01-01

Abstract

The implementation of light-driven catalytic processes in biocatalysis opens a golden window of opportunities. We hereby report the merging of photocatalytic C−C bond formation with enzymatic asymmetric reduction for the direct conversion of simple aldehydes and acrylates or unsaturated carboxylic acids into chiral γ-lactones. Tetrabutylammonium decatungstate (TBADT) is employed as the photocatalyst to trigger the hydroacylation of the starting olefins, yielding the corresponding keto esters/acids. Subsequently, an alcohol dehydrogenase converts the intermediate to the chiral alcohol, which undergoes lactonization to the desired γ-lactone. The photochemoenzymatic synthesis of aliphatic and aromatic γ-lactones was thereby achieved with up to >99 % ee and >99 % yield. This synthesis highlights the power of building molecular complexity by merging photocatalysis with biocatalysis to access high-value added chiral compounds from simple, cheap and largely available starting materials.
2022
The Synthesis of Chiral γ-Lactones by Merging Decatungstate Photocatalysis with Biocatalysis / Feyza Özgen, Fatma; Jorea, Alexandra; Capaldo, Luca; Kourist, Robert; Ravelli, Davide; Schmidt, Sandy. - In: CHEMCATCHEM. - ISSN 1867-3880. - 14:19(2022), pp. e202200855-e202200855. [10.1002/cctc.202200855]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/2961118
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