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

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F12%3A00384909" target="_blank" >RIV/61388963:_____/12:00384909 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201200736" target="_blank" >http://dx.doi.org/10.1002/ejoc.201200736</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201200736" target="_blank" >10.1002/ejoc.201200736</a>

Result language
angličtina
Original language name
General and Efficient a-Oxygenation of Carbonyl Compounds by TEMPO Induced by Single-Electron-Transfer Oxidation of Their Enolates
Original language description
A generally applicable method for the synthesis of protected a-oxygenated carbonyl compounds is reported. It is based on the single-electron-transfer oxidation of easily generated enolates to the corresponding a-carbonyl radicals. Coupling with the stable free radical TEMPO provides a-(piperidinyloxy) ketones, esters, amides, acids or nitriles in moderate-to-excellent yields. Enolate aggregates influence the outcome of the oxygenation reactions significantly. Competitive reactions have been analyzed andconditions for their minimization are presented. Chemoselective reduction of the products led to either NO bond cleavage to a-hydroxy carbonyl compounds or reduction of the carbonyl functionality tomonoprotected 1,2-diols or O-protected amino alcohols.
Czech name
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Czech description
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Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Project
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Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2012
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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