Research Progress in Asymmetric Synthesis of C2 Chiral Indolin-3-ones Involving 2-Substituted-3H-indol-3-ones

doi:10.6023/cjoc202407039

Abstract

Compounds containing 2,2-disubstituted indoline-3-one skeletons are widely used in many fields such as natural products and chiral drugs. The efficient construction of 2,2-disubstituted indolin-3-ones by asymmetric catalysis has attracted more and more attention. The research progress in the asymmetric synthesis of 2,2-disubstituted indolin-3-ones using 2-sub- stituted indolin-3-ones as substrates in recent years is reviewed, including asymmetric aza-Friedel-Crafts reaction, Mannich reaction, aza-Diels-Alder reaction, aza-Henry reaction, aza-Morita-Baylis-Hillman reaction and other reactions. It provides a reference for the future asymmetric synthesis of C2 quaternary carbon center indolin-3-one compounds.

Key words: 2-aryl-3H-indol-3-ones, asymmetric catalysis, C2-quaternary indolin-3-ones

Cite this article

Xiu-Xiu Qiao, Qian Li, Shi'na Zhao, Ruiqi Wei, Tao Ma, Yong-Hui He, Xiao-Jing Zhao. Research Progress in Asymmetric Synthesis of C2 Chiral Indolin-3-ones Involving 2-Substituted-3H-indol-3-ones[J]. Chinese Journal of Organic Chemistry, 2025, 45(4): 1166-1177.

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Fig. & Tab. 24

Figure 1. Natural product molecules containing C2 chiral quaternary carbon indoline-3-one structure

Scheme 1. Asymmetric aza-Friedel-Crafts reaction of spiroindolin-3-ones with indoles

Scheme 2. Asymmetric aza-Friedel-Crafts reaction of 2-aryl- 3H-indole-3-ones and indoles

Scheme 3. Asymmetric aza-Friedel-Crafts reaction of 2-aryl- 3H-indol-3-ones with pyrroles

Scheme 4. Asymmetric aza-Friedel-Crafts reaction of indole- 3-one-2-carboxylate with indole

Scheme 5. Asymmetric aza-Friedel-Crafts reaction of 2-aryl- 3H-indol-3-ones with naphthols

Scheme 6. Asymmetric aza-Friedel-Crafts reaction of 2-aryl- 3H-indol-3-ones with 5-aminopyrazoles

Scheme 7. Asymmetric aza-Friedel-Crafts reactions of 2-aryl-3H-indol-3-ones with 1- and 2-naphthol

Scheme 8. L-Proline-catalyzed asymmetric Mannich reaction of 3H-indole-3-ones with aldehydes and ketones

Scheme 9. Asymmetric Mannich reaction of 2-aryl-3H-indol- 3-ones with simple aldehydes and ketones

Scheme 10. Construction of difluoroalkylated indolin-3-ones by chiral phosphoric acid catalysis

Scheme 11. Asymmetric Mannich reaction of 2-aryl-3H-indol- 3-ones with acetophenones

Scheme 12. Asymmetric Mannich reaction of indole-3-ones with aldehydes and ketones catalyzed by new catalysts

Scheme 13. Asymmetric aza-Diels-Alder reaction of 2-aryl-3H- indol-3-ones with cyclopentadiene catalyzed by Br?nsted acid

Scheme 14. Asymmetric aza-Diels-Alder reaction of 2-aryl- 3H-indol-3-ones with 2,4-dienals

Scheme 15. Proline-catalyzed asymmetric aza-Diels-Alder reaction of 2-aryl-3H-indol-3-ones with cyclic ketenes

Scheme 16. Enantioselective aza-Diels-Alder reaction of 2-aryl- 3H-indol-3-ones with unactivated diene

Scheme 17. B(C6F5)3 and chiral phosphoric acid synergistically catalyzed the asymmetric ketimine-ene reaction of indole-3-ones and α-methylstyrenes

Scheme 18. Synergistic catalysis of metal and Br?nsted acid to construct alkynylindolin-3-ones with quaternary carbon stereocenters at C2 position

Scheme 19. Asymmetric aza-Henry reaction of 2-aryl-3H-indol- 3-ones with nitroalkanes

Scheme 20. Chiral thiourea-catalyzed asymmetric aza-MBH reaction of 2-aryl-3H-indol-3-ones with α,β-unsaturated γ-butyrolactams

Scheme 21. Asymmetric synthesis of 2,2-disubstituted indolin-3-ones with axial and central chirality

Scheme 22. Asymmetric [4＋2] annulation of 2-aryl-3H-indole-3-ones with α,β-unsaturated carboxylic acids catalyzed by a three-component catalyst

Scheme 23. Enantioselective construction of 2,3-dihydro-1H-imidazo [1,5-a]indolin-9(9aH)-ones catalyzed by (R)-CYC-9-CPA

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