Recent Advances in Photocatalytic Deracemization

doi:10.6023/cjoc202207046

Abstract

Chirality is widely found in many natural products and drug molecules. It is of great significance to obtain optically pure chiral compounds because of the fact that different enantiomers have distinct or even opposite physiological activities. Deracemization is the most direct, efficient and atom-economic approach to obtain a single enantiomer, and the emerging photocatalytic deracemization attracts much attention because of its high efficiency. Herein, the recent advances in photocatalytic deracemization are summarized. The future research direction of this field is also prospected.

Key words: deracemization, chiral molecule, asymmetric synthesis, photocatalysis

Cite this article

Yiwen Su, Youquan Zou, Wenjing Xiao. Recent Advances in Photocatalytic Deracemization[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3201-3212.

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Fig. & Tab. 16

Figure 1. The differences among dynamic resolution, dynamic kinetic resolution and deracemization

Figure 2. The thermodynamic and kinetic challenges of deracemization

Figure 3. Four kinds of mechanisms of deracemization

Figure 4. Two strategies for deracemization

Figure 5. Deracemization of axially chiral allenes bearing a six-membered cyclolactam reported by Bach’s group in 2018

Figure 6. Deracemization of axially chiral allenes bearing a five-membered cyclolactam reported by Bach’s group in 2020

Figure 7. Deracemization of acyclic primary allene amides reported by Bach’s group in 2021

Figure 8. Deracemization of axially chiral tetrasubstituted olefins reported by Bach’s group in 2022

Figure 9. Deracemization of 3-cyclopropylquinolones reported by Bach’s group in 2019

Figure 10. Deracemization of spirocyclopropyl indolin-2-ones reported by Bach’s group in 2020

Figure 11. Deracemization of racemic cyclic ureas reported by Knowles & Miller’s group in 2019

Figure 12. Deracemization of hydantoins reported by Bach’s group in 2021

Figure 13. The deracemization of α-branched pyridylketones reported by Meggers & Chen’s group in 2021

Figure 14. Deracemization of α-branched aldehydes reported by Luo’s group in 2022

Figure 15. The deracemization of chiral cyclic sulfoxides reported by Bach’s group in 2019

Figure 16. Deracemization of secondary benzylic alcohols reported by Hu’s group in 2021

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光催化去消旋化的研究进展