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. 2023 Oct 31;3(11):3005-3013.
doi: 10.1021/jacsau.3c00366. eCollection 2023 Nov 27.

Photoredox/Enzymatic Catalysis Enabling Redox-Neutral Decarboxylative Asymmetric C-C Coupling for Asymmetric Synthesis of Chiral 1,2-Amino Alcohols

Yiyin Liu  1   2 , Liangyan Zhu  1   2 , Xuemei Li  1   2 , Yunfeng Cui  1   2 , Atefeh Roosta  1   2 , Jinhui Feng  1   2 , Xi Chen  1   2 , Peiyuan Yao  1   2 , Qiaqing Wu  1   2 , Dunming Zhu  1   2
Affiliations

Photoredox/Enzymatic Catalysis Enabling Redox-Neutral Decarboxylative Asymmetric C-C Coupling for Asymmetric Synthesis of Chiral 1,2-Amino Alcohols

Yiyin Liu et al. JACS Au. .

Abstract

Photocatalysis offers tremendous opportunities for enzymes to access new functions. Herein, we described a redox-neutral photocatalysis/enzymatic catalysis system for the asymmetric synthesis of chiral 1,2-amino alcohols via decarboxylative radical C-C coupling of N-arylglycines and aldehydes by combining an organic photocatalyst, eosin Y, and carbonyl reductase RasADH. Notably, this protocol avoids using any sacrificial reductants. A possible reaction mechanism proposed is that the transformation proceeds through sequential photoinduced decarboxylative radical addition to an aldehyde and a photoenzymatic deracemization pathway. This redox-neutral photoredox/enzymatic strategy is promising not only for effective synthesis of a series of chiral amino alcohols in a green and sustainable manner but also for the design of other novel C-C radical coupling transformations for the synthesis of bioactive molecules.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Previous Studies on Photoenzymatic C–C Bond Formation and This Work
Figure 1
Figure 1
Yield and enantiomeric excess of product 3ba over time.
Scheme 2
Scheme 2. (a–f) Mechanism Studies and Synthetic Application
Figure 2
Figure 2
Possible reaction mechanism.
See this image and copyright information in PMC

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References

    1. Lee S. H.; Choi D. S.; Kuk S. K.; Park C. B. Photobiocatalysis: Activating Redox Enzymes by Direct or Indirect Transfer of Photoinduced Electrons. Angew. Chem., Int. Ed. 2018, 57, 7958–7985. 10.1002/anie.201710070. - DOI - PubMed
    1. Zhang S.; Liu S.; Sun Y.; Li S.; Shi J.; Jiang Z. Enzyme-photo-coupled Catalytic Systems. Chem. Soc. Rev. 2021, 50, 13449–13466. 10.1039/D1CS00392E. - DOI - PubMed
    1. Özgen F. F.; Runda M. E.; Schmidt S. Photo-biocatalytic Cascades: Combining Chemical and Enzymatic Transformations Fueled by Light. ChemBioChem. 2021, 22, 790–806. 10.1002/cbic.202000587. - DOI - PMC - PubMed
    1. Hall M. Enzymatic Strategies for Asymmetric Synthesis. RSC Chem. Biol. 2021, 2, 958–989. 10.1039/D1CB00080B. - DOI - PMC - PubMed
    1. Wu S.; Snajdrova R.; Moore J. C.; Baldenius K.; Bornscheuer U. T. Biocatalysis: Enzymatic Synthesis for Industrial Applications. Angew. Chem., Int. Ed. 2021, 60, 88–119. 10.1002/anie.202006648. - DOI - PMC - PubMed