Epoxidation and Baeyer–Villiger oxidation of γ-hydroxy-αβ-unsaturated ketones on exposure to m-chloroperbenzoic acid

1992 ◽  
pp. 1735-1740 ◽  
Author(s):  
Marioara Mendelovici ◽  
Erwin Glotter
Keyword(s):  
Unsaturated Ketones ◽  
Villiger Oxidation

Synthetic application of cyclobutanes V. α-Carbalkoxymethylation of α, β-unsaturated ketones

1977 ◽  
Vol 55 (5) ◽  
pp. 822-830 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Patrick Chi-Lin Yao
Keyword(s):  
Hydrogen Peroxide ◽  
Acetic Acid ◽  
Acetic Anhydride ◽  
Potassium Carbonate ◽  
Alkyl Iodide ◽  
Keto Ester ◽  
Unsaturated Ketones ◽  
Synthetic Application ◽  
Hydrolysis Of ◽  
Villiger Oxidation

Two general methods for α-carbalkoxymethylation of both enolizable and nonenolizable (towards the γ-position) α,β-unsaturated ketones have been developed. Method A involves three synthetic steps: photocycloaddition of the starting enone to 1,1-dimethoxyethylene, hydrolysis–oxidation of the adduct with acetic acid and 30% hydrogen peroxide, and O-alkylation of the resulting mixture of lactone and acid using anhydrous potassium carbonate and an alkyl iodide, e.g., 13 → 17 → 21 + 22 → 23. Method B differs from method A in the means of securing the required cyclobutanone intermediate. Thus, photocycloaddition of 13 to vinyl acetate followed by hydrolysis of the adduct gave two epimeric keto alcohols 39 whose oxidation with dimethyl sulfoxide and acetic anhydride afforded diketone 40. Baeyer–Villiger oxidation of 40 followed by methylation of the products 21 and 22 completed the overall α-carbomethoxymethylation process to give keto ester 23.

ChemInform Abstract: Organoselenium-Catalyzed Baeyer-Villiger Oxidation of α,β-Unsaturated Ketones by Hydrogen Peroxide to Access Vinyl Esters.

ChemInform ◽  
2015 ◽  
Vol 46 (29) ◽  
pp. no-no
Author(s):  
Xu Zhang ◽  
Jianqing Ye ◽  
Lei Yu ◽  
Xinkang Shi ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Vinyl Esters ◽  
Unsaturated Ketones ◽  
Villiger Oxidation

Organoselenium-Catalyzed Baeyer-Villiger Oxidation of α,β-Unsaturated Ketones by Hydrogen Peroxide to Access Vinyl Esters

2015 ◽  
Vol 357 (5) ◽  
pp. 955-960 ◽  
Author(s):  
Xu Zhang ◽  
Jianqing Ye ◽  
Lei Yu ◽  
Xinkang Shi ◽  
Ming Zhang ◽  
...  
Keyword(s):  
Hydrogen Peroxide ◽  
Vinyl Esters ◽  
Unsaturated Ketones ◽  
Villiger Oxidation

1,4-Reductions of α,β-Unsaturated Ketones and Aldehydes via in situ Generated Hydridocuprates

Synlett ◽  
1989 ◽  
Vol 1989 (01) ◽  
pp. 64-66 ◽  
Author(s):  
Bruce H. Lipshutz ◽  
Christopher S. Ung ◽  
Saumitra Sengupta
Keyword(s):  
Unsaturated Ketones
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