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Search for "3-hydroxyoxindoles" in Full Text gives 2 result(s) in Beilstein Journal of Organic Chemistry.
Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update
- Bin Yu,
- Hui Xing,
- De-Quan Yu and
- Hong-Min Liu
Beilstein J. Org. Chem. 2016, 12, 1000–1039, doi:10.3762/bjoc.12.98
- , enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the
- last decades. Additionally, 3-hydroxyoxindoles as versatile precursors have also been used in the total synthesis of natural products and for constructing structurally novel scaffolds. In this review, we aim to provide an overview about the catalytic asymmetric synthesis of biologically important 3
- -substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations. Keywords: 3-hydroxyoxindoles; oxindoles; organocatalysis; spirooxindoles; transition metal catalysis; Introduction Chiral oxindoles are an important class of compounds, which widely exist in nature and have exhibited diverse
Graphical Abstract
Figure 1: 3-Hydroxyoxindole-containing natural products and biologically active molecules.
Scheme 1: Chiral CNN pincer Pd(II) complex 1 catalyzed asymmetric allylation of isatins.
Scheme 2: Asymmetric allylation of ketimine catalyzed by the chiral CNN pincer Pd(II) complex 2.
Scheme 3: Pd/L1 complex-catalyzed asymmetric allylation of 3-O-Boc-oxindoles.
Scheme 4: Cu(OTf)2-catalyzed asymmetric direct addition of acetonitrile to isatins.
Scheme 5: Chiral tridentate Schiff base/Cu complex catalyzed asymmetric Friedel–Crafts alkylation of isatins ...
Scheme 6: Guanidine/CuI-catalyzed asymmetric alkynylation of isatins with terminal alkynes.
Scheme 7: Asymmetric intramolecular direct hydroarylation of α-ketoamides.
Scheme 8: Plausible catalytic cycle for the direct hydroarylation of α-ketoamides.
Scheme 9: Ir-catalyzed asymmetric arylation of isatins with arylboronic acids.
Scheme 10: Enantioselective decarboxylative addition of β-ketoacids to isatins.
Scheme 11: Ruthenium-catalyzed hydrohydroxyalkylation of olefins and 3-hydroxy-2-oxindoles.
Scheme 12: Proposed catalytic mechanism and stereochemical model.
Scheme 13: In-catalyzed allylation of isatins with stannylated reagents.
Scheme 14: Modified protocol for the synthesis of allylated 3-hydroxyoxindoles.
Scheme 15: Hg-catalyzed asymmetric allylation of isatins with allyltrimethylsilanes.
Scheme 16: Enantioselective additions of organoborons to isatins.
Scheme 17: Asymmetric aldol reaction of isatins with cyclohexanone.
Scheme 18: Enantioselective aldol reactions of aliphatic aldehydes with isatin derivatives and the plausible t...
Scheme 19: Enantioselective aldol reaction of isatins and 2,2-dimethyl-1,3-dioxan-5-one.
Scheme 20: Asymmetric aldol reactions between ketones and isatins.
Scheme 21: Phenylalanine lithium salt-catalyzed asymmetric synthesis of 3-alkyl-3-hydroxyoxindoles.
Scheme 22: Aldolization between isatins and dihydroxyacetone derivatives.
Scheme 23: One-pot asymmetric synthesis of convolutamydine A.
Scheme 24: Asymmetric aldol reactions of cyclohexanone and acetone with isatins.
Scheme 25: Aldol reactions of acetone with isatins.
Scheme 26: Aldol reactions of ketones with isatins.
Scheme 27: Enantioselective allylation of isatins.
Scheme 28: Asymmetric aldol reaction of trifluoromethyl α-fluorinated β-keto gem-diols with isatins.
Scheme 29: Plausible mechanism proposed for the asymmetric aldol reaction.
Scheme 30: Asymmetric aldol reaction of 1,1-dimethoxyacetone with isatins.
Scheme 31: Enantioselective Friedel-Crafts reaction of phenols with isatins.
Scheme 32: Enantioselective addition of 1-naphthols with isatins.
Scheme 33: Enantioselective aldol reaction between 3-acetyl-2H-chromen-2-ones and isatins.
Scheme 34: Stereoselective Mukaiyama–aldol reaction of fluorinated silyl enol ethers with isatins.
Scheme 35: Asymmetric vinylogous Mukaiyama–aldol reaction between 2-(trimethylsilyloxy)furan and isatins.
Scheme 36: β-ICD-catalyzed MBH reactions of isatins with maleimides.
Scheme 37: β-ICD-catalyzed MBH reactions of 7-azaisatins with maleimides and activated alkenes.
Scheme 38: Enantioselective aldol reaction of isatins with ketones.
Scheme 39: Direct asymmetric vinylogous aldol reactions of allyl ketones with isatins.
Scheme 40: Enantioselective aldol reactions of ketones with isatins.
Scheme 41: The MBH reaction of isatins with α,β-unsaturated γ-butyrolactam.
Scheme 42: Reactions of tert-butyl hydrazones with isatins followed by oxidation.
Scheme 43: Aldol reactions of isatin derivatives with ketones.
Scheme 44: Enantioselective decarboxylative cyanomethylation of isatins.
Scheme 45: Catalytic kinetic resolution of 3-hydroxy-3-substituted oxindoles.
Scheme 46: Lewis acid catalyzed Friedel–Crafts alkylation of 3-hydroxy-2-oxindoles with electron-rich phenols.
Scheme 47: Lewis acid catalyzed arylation of 3-hydroxyoxindoles with aromatics.
Scheme 48: Synthetic application of 3-arylated disubstituted oxindoles in the construction of core structures ...
Scheme 49: CPA-catalyzed dearomatization and arylation of 3-indolyl-3-hydroxyoxindoles with tryptamines and 3-...
Scheme 50: CPA-catalyzed enantioselective decarboxylative alkylation of β-keto acids with 3-hydroxy-3-indolylo...
Scheme 51: BINOL-derived imidodiphosphoric acid-catalyzed enantioselective Friedel–Crafts reactions of indoles...
Scheme 52: CPA-catalyzed enantioselective allylation of 3-indolylmethanols.
Scheme 53: 3-Indolylmethanol-based substitution and cycloaddition reactions.
Scheme 54: CPA-catalyzed asymmetric [3 + 3] cycloaddtion reactions of 3-indolylmethanols with azomethine ylide...
Scheme 55: CPA-catalyzed three-component cascade Michael/Pictet–Spengler reactions of 3-indolylmethanols and a...
Scheme 56: Acid-promoted chemodivergent and stereoselective synthesis of diverse indole derivatives.
Scheme 57: CPA-catalyzed asymmetric formal [3 + 2] cycloadditions.
Scheme 58: CPA-catalyzed enantioselective cascade reactions for the synthesis of C7-functionlized indoles.
Scheme 59: Lewis acid-promoted Prins cyclization of 3-allyl-3-hydroxyoxindoles with aldehydes.
Scheme 60: Ga(OTf)3-catalyzed reactions of allenols and phenols.
Scheme 61: I2-catalyzed construction of pyrrolo[2.3.4-kl]acridines from enaminones and 3-indolyl-3-hydroxyoxin...
Scheme 62: CPA-catalyzed asymmetric aza-ene reaction of 3-indolylmethanols with cyclic enaminones.
Scheme 63: Asymmetric α-alkylation of aldehydes with 3-indolyl-3-hydroxyoxindoles.
Scheme 64: Organocatalytic asymmetric α-alkylation of enolizable aldehydes with 3-indolyl-3-hydroxyoxindoles a...
Organocatalytic asymmetric Michael addition of unprotected 3-substituted oxindoles to 1,4-naphthoquinone
- Jin-Sheng Yu,
- Feng Zhou,
- Yun-Lin Liu and
- Jian Zhou
Beilstein J. Org. Chem. 2012, 8, 1360–1365, doi:10.3762/bjoc.8.157
- biological activities [4]. Accordingly, the development of efficient synthetic methods to enable the synthesis of 3,3-disubstituted oxindoles in great structural diversity is of current interest, and much progress had been made in the catalytic enantioselective synthesis of 3-hydroxyoxindoles [5][6][7][8][9
- enantioenriched 3-hydroxyoxindoles [22][23][24]. For the synthesis of chiral 3-aminooxindoles, we developed the first example of catalytic asymmetric addition of nucleophiles to isatin-derived ketoimines using TMSCN [25] and the amination of unprotected 3-prochiral oxindoles using di-tert-butyl azodicarboxylate
Graphical Abstract
Figure 1: Cinchona alkaloid-derived catalysts screened for condition optimization (Table 1).
Scheme 1: A one-pot synthesis of enantioenriched 3,3-diaryloxindoles.
