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Intramolecular aldol condensation

11 real reactions from the literature, on methyl ketones, aryl ketones and dialkyl ketones. Each scheme shows starting materials, conditions and products, with the yield and reference where the source reports them.

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  1. Intramolecular aldol: (4R)-4-ethyl-6-oxoheptanal (a methyl ketone) with NaOH; Et2O / H2O gives (4S)-4-ethyl-2-methylcyclopentene-1-carbaldehyde (the cyclic enone). 85% yield.
    Intramolecular aldolEur. J. Org. Chem. 2001, 2435

  2. Intramolecular aldol: 2-(2-acetylphenyl)benzaldehyde (an aryl ketone) with 1) cat. TsOH EtOH/H2O; 1 min / RT; 2) then add NaOH; 10 min / 70 ºC gives 5H-dibenzo(a,c)cyclohepten-5-one (the cyclic enone). 99% yield.
    Intramolecular aldolJ. Org. Chem. 2009, 74, 3948

  3. Intramolecular aldol: a methyl ketone with NaOH; MeOH / RT gives the cyclic enone. 90% yield.
    Intramolecular aldolAngew. Chem. Int. Ed. 2011, 50, 5878

  4. Intramolecular aldol: 2-(3-oxobutyl)isoindoline-1,3-dione (a methyl ketone) with TfOH; PhMe gives 3,4-dihydropyrido[1,2-b]isoindole-2,6-dione (the cyclic enone). 94% yield.
    Intramolecular aldolOrg. Lett. 2020, 22, 239

  5. Intramolecular aldol: a methyl ketone with 1) KOH; MeOH / H2O; 3 h / RT; 2) MsCl / Et3N; CH2Cl2 gives the cyclic enone. 99% yield.
    Intramolecular aldolCan. J. Chem. 1986, 64, 1404

  6. Intramolecular aldol: a methyl ketone with 1) KOH, MeOH / H2O, 3 h / RT; 2) MsCl / Et3N, CH2Cl2 gives the cyclic enone.
    Intramolecular aldolCan. J. Chem. 1986, 64, 1404

  7. Intramolecular aldol: a methyl ketone with KOH, MeOH / H2O, 2 h / RT gives the cyclic enone.
    Intramolecular aldolPCT Int. Appl. WO2014070915

  8. Intramolecular aldol: a methyl ketone with NaOH, MeOH / H2O, 20 min / RT gives the cyclic enone. 90% yield.
    Intramolecular aldolAngew. Chem. Int. Ed. 2011, 50, 5878

  9. Intramolecular aldol: a methyl ketone with NaOH, H2O, 10 min / RT gives the cyclic enone. 52% yield.
    Intramolecular aldolChem. Eur. J. 2012, 18, 12498

  10. Intramolecular aldol: 2-(2-acetylphenyl)benzaldehyde (an aryl ketone) with 1) cat. TsOH, EtOH/H2O, 1 min / RT; 2) then add NaOH, 10 min / 70 C gives 5H-dibenzo(a,c)cyclohepten-5-one (the cyclic enone). 99% yield.
    Intramolecular aldolJ. Org. Chem. 2009, 74, 3948

  11. Intramolecular aldol: a dialkyl ketone with KOH gives the cyclic enone.
    Intramolecular aldolJ. Org. Chem. 1973, 38, 3663