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.
Original language | English |
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Article number | e202200855 |
Journal | ChemCatChem |
Volume | 14 |
Issue number | 19 |
DOIs | |
Publication status | Published - 10 Oct 2022 |
Keywords
- alcohol dehydrogenases
- asymmetric reduction
- C−C bond formation
- decatungstate anion
- photobiocatalysis
ASJC Scopus subject areas
- Catalysis
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry