Реферат: Malonyl peroxides act both as oxidants and reagents for C−O coupling in reactions with methyl and silyl enol ethers. In the proposed conditions, the oxidative C−O coupling of malonyl peroxides with enol ethers selectively proceeds, bypassing the traditional Rubottom hydroxylation of enol ethers by peroxides. It was observed that the oxidative [5+2] cycloaddition of malonyl peroxides and enol ethers is the key stage of the discovered process. Oxidative C−O coupling of silyl enol ethers leads to the formation of α-acyloxyketones with a free carboxylic acid group. A specially developed preparative one-pot procedure transforms ketones via silyl enol ethers formation and the following coupling into α-acyloxyketones with yields 35–88%. The acid-catalyzed coupling with methyl enol ethers gives remarkable products while retaining the easily oxidizable enol fragment. Furthermore, these molecules contain a free carboxylic acid group, thus these nontrivial products contain two usually incompatible acid and enol ether groups.

Библиографическая ссылка: Vil' V.A. , Gorlov E.S. , Bityukov O.V. , Barsegyan Y.A. , Romanova Y.E. , Merkulova V.M. , Terent'ev A.O.
C−O coupling of Malonyl Peroxides with Enol Ethers via [5+2] Cycloaddition: Non‐Rubottom Oxidation
Advanced Synthesis & Catalysis. 2019. V.361. N13. P.3173-3181. DOI: 10.1002/adsc.201900271 WOS Scopus OpenAlex

Идентификаторы БД:

Web of science:	WOS:000484142600017
Scopus:	2-s2.0-85065328673
OpenAlex:	W2935308669

Цитирование в БД:

БД	Цитирований
OpenAlex	17
Scopus	18

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