Oxone-promoted hydration of electron-deficient allenic esters and ketones into 1,3-dicarbonyl compounds

• Published in: Tetrahedron letters Vol. 56; no. 30; pp. 4523 - 4526
• Main Authors: Yi, Yu-Ping, Zheng, Yan, Nie, Jing, Ma, Jun-An
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 22-07-2015
• Subjects: 1,3-Dicarbonyl compounds; Allenoate; Hydration; N,N-Dimethylformamide; Oxone; Hydration; 1,3-Dicarbonyl compounds; Oxone; Allenoate; N,N-Dimethylformamide
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2015.05.120

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A novel and mild protocol for the hydration of electron-deficient allenic esters and ketones into various 1,3-dicarbonyl compounds is described. The hydration of allenes promoted by oxone in DMF afforded the corresponding products in moderate to good yields. This work features the employment of only a catalytic amount of inexpensive and nontoxic solid reagent oxone (2KHSO5·KHSO4·K2SO4), avoiding the utility of toxic metals or traditional Brønsted acids, in a green version of viewpoint. A possible reaction mechanism for this transformation is also primarily proposed.