4.8 Article

Enantiocomplementary decarboxylative hydroxylation combining photocatalysis and whole-cell biocatalysis in a one-pot cascade process

Journal

GREEN CHEMISTRY
Volume 21, Issue 8, Pages 1907-1911

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c9gc00098d

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Funding

  1. National Natural Science Foundation of China [21574113, 21472169]
  2. Zhejiang Provincial Natural Science Foundation [LY19B020014]
  3. Fundamental Research Funds for the Central Universities [2018QNA3010]

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Designing a green, highly efficient and stereoselective catalytic system to generate valuable enantioenriched products is a long-standing goal in green chemistry. Here, we report a one-pot cascade combining photocatalysts with (R)- or (S)-selective ketoreductases for the decarboxylative carbonylation of carboxylic acids and the subsequent bioreduction to generate valuable chiral alcohols. Using this approach, various chiral alcohols with complementary (R)- or (S)-configurations were prepared with good yields (up to 93%) and excellent stereoselectivity (up to 99% ee). Such a photochemo-enzymatic one-pot whole-cell process combines the advantages of both photocatalysts and enzyme catalysts and provides a mild, green, metal-free and highly stereoselective alternative in asymmetric decarboxylative hydroxylation reactions.

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