Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids

doi:10.6023/cjoc202205032

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (10): 3335-3350.DOI: 10.6023/cjoc202205032 Previous Articles Next Articles

Special Issue: 不对称催化专辑

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手性Lewis酸催化的可见光不对称合成研究进展

成秀亮^a, 李冬^a, 杨博轩^a, 林玉妹^a, 龚磊^a^,^b^,^*()

a 厦门大学化学化工学院福建省化学生物学重点实验室福建厦门 361005
b 福建省能源材料科学与技术创新实验室(IKKEM) 福建厦门 361005

收稿日期:2022-05-19 修回日期:2022-06-25 发布日期:2022-11-02
通讯作者: 龚磊
作者简介:
†共同第一作者.
基金资助:
国家自然科学基金(22071209); 国家自然科学基金(22071206); 及国家高层次青年人才资助项目

Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids

Xiuliang Cheng^a, Dong Li^a, Boxuan Yang^a, Yumei Lin^a, Lei Gong^a^,^b()

a College of Chemistry and Chemical Engineering, Key Laboratory of Chemical Biology of Fujian Province, Xiamen University, Xiamen, Fujian 361005
b Innovation Laboratory for Sciences and Technologies of Energy Materials of Fujian Province (IKKEM), Xiamen, Fujian 361005

Received:2022-05-19 Revised:2022-06-25 Published:2022-11-02
Contact: Lei Gong
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(22071209); National Natural Science Foundation of China(22071206); National Youth Talent Support Program

In recent years, visible-light photocatalytic asymmetric synthesis has shown considerable potential in the mild and rapid construction of optically active organic molecules with structural diversity. Chiral Lewis acids (CLA), including chiral borane compounds, lanthanum complexes, first-row transition metal complexes, and chiral-at-iridium or rhodium complexes, have been established as one class of the most effective catalysts being capable of controlling the stereochemistry in photo-induced chemical transformations. The recent advances in this emerging field were presented by classifying the reactions into bifunctional CLA photocatalytic reactions and reactions enabled by dual catalysis with a CLA catalyst and an external photosensitizer, expecting that these studies will stimulate progress in organic synthesis, photocatalysis and asymmetric catalysis.

Key words: visible light photocatalysis, asymmetric synthesis, chiral Lewis acid, cooperative catalysis, bifunctional catalysis

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Xiuliang Cheng, Dong Li, Boxuan Yang, Yumei Lin, Lei Gong. Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3335-3350.

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Fig. & Tab. 26

Scheme 1. Photocatalytic diastereo-, enantioselective [2+2] cycloaddition enabled by a chiral borane Lewis acid

Scheme 2. Enantioselective rearrangements reaction enabled by a chiral borane Lewis acid

Scheme 3. Chiral borane Lewis acid-catalyzed enantioselective addition of α,β-unsaturated carbonyl compounds via EDA complexes

Scheme 4. Photocatalytic enantioselective α-alkylation reaction of ketones enabled by a chiral-at-iridium octahedral Lewis acid

Scheme 5. Other photochemical asymmetric reactions enabled by bifunctional chiral-at-iridium Lewis acids

Scheme 6. Design of a chiral-at-rhodium Lewis acid and its applications

Scheme 7. Design of a chiral-at-rhodium Lewis acid with a new cyclometalating ligand and its applications

Scheme 8. Photocatalytic deracemization enabled by a chiral-at-rhodium Lewis acid

Scheme 9. Photocatalytic asymmetric [2+2] cycloaddition enabled by a chiral-at-rhodium Lewis acid

Scheme 10. photocatalytic asymmetric cycloaddition enabled by a chiral-at-rhodium Lewis acid

Scheme 11. Design of a bifunctional chiral nickel Lewis acid and its application to photocatalytic enantioselective aerobic oxidation of β-ketoesters

Scheme 12. Photocatalytic asymmetric synthesis enabled by a chiral bisoxazoline-nickel catalyst

Scheme 13. Photocatalytic enantioselective alkylation reaction of imines enabled by a chiral bisoxazoline-copper(II) catalyst

Scheme 14. Other photocatalytic asymmetric reactions enabled by a chiral bisoxazoline-copper(II) catalyst

Scheme 15. Photocatalytic asymmetric [2+2] cycloaddition reaction enabled by dual catalysis with a lanthanide-based chiral Lewis acid and a photocatalyst

Scheme16. Other photocatalytic asymmetric reactions enabled by dual catalysis with a lanthanide-based chiral Lewis acid and a photocatalyst

Scheme 17. Photocatalytic asymmetric [3+2] cycloaddition enabled by merging a gadolinium-based chiral Lewis acid and a ruthenium bipyridine complex

Scheme 18. Asymmetric α-amination and α-alkylation reactions enabled by dual catalysis with a chiral-at-rhodium Lewis acid and an external photocatalyst

Scheme 19. Dual catalysis enabled by a chiral-at-rhodium Lewis acid and an organophotocatalyst

Scheme 20. A variety of photocatalytic asymmetric reactions enabled by dual catalysis with a chiral-at-rhodium Lewis acid and an external photocatalyst

Scheme 21. Photocatalytic enantioselective di/perfluoroalkylation enabled by synergistic catalysis with a photoredox catalyst and a chiral nickel Lewis acid

Scheme 22. Photocatalytic enantioselective synthesis of chiral amino- alcohol derivatives enabled by synergistic catalysis

Scheme 23. Synergistic catalysis with an octahedral chiral cobalt Lewis acid and an organocatalyst for a photocatalytic asymmetric Giese reaction

Scheme 24. Photocatalytic enantioselective aminomethylation reaction enabled by dual catalysis with a copper-based chiral Lewis acid and an Ir photocatalyst

Scheme 25. Photocatalytic region and stereoselective C(sp3)—H functionalization enabled by dual HAT photocatalysis and chiral copper Lewis acid-based catalysis

Scheme 26. Photocatalytic three-component asymmetric C (sp3)-H sulfonylation enabled by dual HAT photocatalysis and chiral nickel Lewis acid-based catalysis

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手性Lewis酸催化的可见光不对称合成研究进展

Recent Advances in Visible-Light Photocatalytic Asymmetric Synthesis Enabled by Chiral Lewis Acids

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Fig. & Tab. 26

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