光催化去消旋化的研究进展

doi:10.6023/cjoc202207046

摘要/Abstract

手性广泛存在于众多天然产物和药物分子中, 由于对映体之间具有不同甚至是相反的生理活性, 获得光学纯的手性化合物具有重要的研究意义. 去消旋化是获得单一对映体最直接、最有效和最原子经济的途径, 而新兴的光催化去消旋化由于其高效性更是备受瞩目. 综述了光催化去消旋化最新的研究进展, 并对该领域未来的研究前景进行了展望.

关键词: 去消旋化, 手性分子, 不对称合成, 光催化

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

引用此文

苏艺雯, 邹有全, 肖文精. 光催化去消旋化的研究进展[J]. 有机化学, 2022, 42(10): 3201-3212.

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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图/表 16

图1. 动力学拆分、动态动力学拆分和去消旋化的区别

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

图2. 去消旋化的热力学和动力学挑战

Figure 2. The thermodynamic and kinetic challenges of deracemization

图3. 去消旋化的四种机制

Figure 3. Four kinds of mechanisms of deracemization

图4. 去消旋化的两种主要策略

Figure 4. Two strategies for deracemization

图5. Bach课题组在2018年报道的轴手性联烯六元环内酰胺的去消旋化

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

图6. Bach课题组在2020年报道的轴手性联烯五元环内酰胺的去消旋化

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

图7. Bach课题组在2021年报道的非环状一级联烯酰胺的去消旋化

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

图8. Bach课题组在2022年报道的轴手性四取代烯烃的去消旋化

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

图9. Bach课题组在2019年报道的3-环丙烷喹啉酮的去消旋化

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

图10. Bach课题组在2020年报道的螺环丙烷基吲哚-2-酮的去消旋化

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

图11. Knowles & Miller课题组在2019年报道的外消旋环脲化合物的去消旋化

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

图12. Bach课题组在2021年报道的乙内酰脲类化合物的去消旋化

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

图13. Meggers & Chen课题组在2021年报道的α-支链吡啶酮的去消旋化

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

图14. Luo课题组在2022年报道的α-支链醛的去消旋化

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

图15. Bach课题组在2019年报道的手性环状亚砜类化合物的去消旋化

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

图16. Hu课题组在2021年报道的二级醇的去消旋化

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

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