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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_x - Nezařazeno - Článek v odborném periodiku (Jimp, Jsc a Jost)

CEP obor

CC - Organická chemie

OECD FORD obor

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Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2012

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

European Journal of Organic Chemistry

ISSN

1434-193X

e-ISSN

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Svazek periodika

—

Číslo periodika v rámci svazku

24

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

22

Strana od-do

4461-4482

Kód UT WoS článku

000307497600004

EID výsledku v databázi Scopus

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