General and Efficient α??Oxygenation of Carbonyl Compounds by TEMPO Induced by Single??Electron??Transfer Oxidation of Their Enolates

E Dinca, P Hartmann, J Smrček, I Dix…

文献索引：Dinca, Emanuela; Hartmann, Philip; Smrcek, Jakub; Dix, Ina; Jones, Peter G.; Jahn, Ullrich European Journal of Organic Chemistry, 2012 , # 24 p. 4461 - 4482

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被引用次数: 16

摘要

Abstract A generally applicable method for the synthesis of protected α-oxygenated carbonyl compounds is reported. It is based on the single-electron-transfer oxidation of easily generated enolates to the corresponding α-carbonyl radicals. Coupling with the stable free radical TEMPO provides α-(piperidinyloxy) ketones, esters, amides, acids or nitriles in moderate-to-excellent yields. Enolate aggregates influence the outcome of the ...