Research Progress of Reactions Participated by α-Hydroxy Ketones

doi:10.6023/cjoc202203007

Abstract

α-Hydroxyl ketones are an important class of compounds. They are not only the key structural fragments of many biologically active natural products, but also the important synthetic building blocks, hence α-hydroxyl ketones are employed in the synthesis of various biologically active molecules and drugs. The nucleophilic addition reactions and the cycloaddition reactions involving α-hydroxyl ketones are sorted out and summarized.

Key words: α-hydroxyl ketone, nucleophilic addition reaction, cycloaddition reaction

Cite this article

Junjiao Wang, Yuyu Lv, Yongwei Shang, Zhenli Cui, Ke-Hu Wang, Danfeng Huang, Yulai Hu. Research Progress of Reactions Participated by α-Hydroxy Ketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2300-2321.

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Fig. & Tab. 63

Scheme 1. Synthesis of α-primary hydroxyketones with methyl ketones as substrates

Scheme 2. Synthesis of α-primary hydroxyketones with methyl ketones as substrates

Scheme 3. Synthesis of α-primary hydroxyketones with olefins as substrates

Scheme 4. Synthesis of α-primary hydroxyketones with aldehydes as substrates

Scheme 5. Synthesis of α-primary hydroxyketones with 1,2-dihydroxy compounds as substrates

Scheme 6. Synthesis of α-secondary hydroxyketones from alcohols or enol compounds

Scheme 7. Synthesis of α-secondary hydroxyketones through oxidation of alcohols or enol compounds

Scheme 8. Synthesis of α-secondary hydroxyketones through reduction of alkynes

Scheme 9. Synthesis of α-secondary hydroxyketones through rearrangement reaction of α-hydroxy esters

Scheme 10. Synthesis of α-tertiary hydroxyketones through oxidation of carbonyl compounds

Scheme 11. Synthesis of α-tertiary hydroxyketones through oxidation of carbonyl compounds

Scheme 12. Synthesis of α-tertiary hydroxyketones through oxidation of carbonyl compouns

Scheme 13. Synthesis of α-tertiary hydroxyketones through oxidation of alkynyl alcohol compounds

Scheme 14. Asymmetric aldol reaction of α-hydroxyl ketones with aldehydes

Scheme 15. Asymmetric aldol reaction of α-hydroxyl ketones with aldehydes

Scheme 16. Asymmetric aldol reaction of α-hydroxyl ketones with aldehydes

Scheme 17. Cycloaddition reaction of α-hydroxyl ketones with ethyl glyoxylates

Scheme 18. Asymmetric Mannich reaction of α-hydroxyl ketones with imines

Scheme 19. Asymmetric Mannich reaction of α-hydroxyl ketones with imines

Scheme 20. Asymmetric Mannich reaction of α-hydroxyl ketones with indigo imines

Scheme 21. Cross dehydrogenation coupling reaction of α-hydroxyl ketones with N-arylglycine esters

Scheme 22. Cross dehydrogenation coupling reaction of α-hydroxyl ketones with N-arylglycine esters

Scheme 23. Asymmetric Michael reaction of α-hydroxyl ketones with nitroolefins

Scheme 24. Asymmetric Michael reaction of α-hydroxyl ketones with nitroolefins

Scheme 25. Asymmetric Michael reaction of α-hydroxyl ketones with olefins

Scheme 26. Asymmetric Michael reaction of α-hydroxy indanones with olefins

Scheme 27. Asymmetric Michael reaction of α-hydroxyl ketones with p-methylene benzoquinones

Scheme 28. Cycloaddition reaction of α-hydroxyl ketones with cyanamide

Scheme 29. Cycloaddition reaction of α-hydroxyl ketones with cyanamide

Scheme 30. Cycloaddition reaction of α-hydroxyl ketones with α-cyanamides

Scheme 31. Cycloaddition reaction of α-hydroxyl ketones with nitriles

Scheme 32. Cycloaddition reaction of α-hydroxyl ketones with nitriles

Scheme 33. Cycloaddition reactions of α-hydroxyl ketones with nitriles

Scheme 34. Cycloaddition reaction of α-hydroxyl ketones with potassium thiocyanate

Scheme 35. Cycloaddition reaction of α-hydroxyl ketones with isocyanates

Scheme 36. Cycloaddition reaction of α-hydroxyl ketones with isocyanates

Scheme 37. Cycloaddition reaction of α-hydroxyl ketones with alkynes

Scheme 38. Cycloaddition reaction of α-hydroxyl ketones with alkynes

Scheme 39. Cycloaddition reaction of α-hydroxyl ketones with alkynes

Scheme 40. Cycloaddition reaction of α-hydroxyl ketones with Mercaptan esters

Scheme 41. Cycloaddition reaction of α-hydroxyl ketones with diamine compounds

Scheme 42. Cycloaddition reaction of α-hydroxyl ketones with O-phenylenediamine compounds

Scheme 43. Cycloaddition reaction of α-hydroxyl ketones with O-phenylenediamine compounds

Scheme 44. Cycloaddition reaction of α-hydroxyl ketones with 2-vinyl ketone

Scheme 45. Cycloaddition reaction of α-hydroxyl ketones with ketene derivatives

Scheme 46. Cycloaddition reaction of α-hydroxyl ketones with ketene derivatives

Scheme 47. Cycloaddition reaction of α-hydroxyl ketones with esters

Scheme 48. Cycloaddition reaction of 3-hydroxyindole ketones with α,β-unsaturated esters

Scheme 49. Cycloaddition reaction of α-hydroxyl ketones with β,γ-unsaturated-α-ketone esters

Scheme 50. Cycloaddition reaction of α-hydroxy-1-windanones with α,β-unsaturated esters

Scheme 51. Cycloaddition reaction of α-hydroxy-1-indanones with β,γ-unsaturated α-ketoamides

Scheme 52. Cycloaddition reaction of α-hydroxy-1-indanones with o-ester chalcones

Scheme 53. Cycloaddition reaction of α-hydroxyl ketones with β,γ-unsaturated α-ketoamides

Scheme 54. Cycloaddition reaction of α-hydroxyl ketones with β,γ-unsaturated α-ketoamides

Scheme 55. Cycloaddition reaction of α-hydroxyl ketones with resorcinol derivatives

Scheme 56. Cycloaddition reaction of α-hydroxyl ketones with O-hydroxyacetophenone derivatives

Scheme 57. Cycloaddition reaction of α-hydroxyl ketones with ammonium acetate

Scheme 58. Cycloaddition reaction of α-hydroxyl ketones with ammonium sulfonamides

Scheme 59. Three tomponent cycloaddition reaction involving α-hydroxyl ketones

Scheme 60. Cycloaddition reaction of α-hydroxy-1-indanones with alkylene nitrogen lactones

Scheme 61. Oxidative coupling reaction of α-hydroxyl ketones with alkynes

Scheme 62. Cross coupling reaction of α-hydroxyl ketones with cyclopropanes

Scheme 63. Rearrangement of α-hydroxyl ketones

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