Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F12%3A10127547" target="_blank" >RIV/00216208:11310/12:10127547 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/12:00378614
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201200077" target="_blank" >http://dx.doi.org/10.1002/ejoc.201200077</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201200077" target="_blank" >10.1002/ejoc.201200077</a>

Result language
angličtina
Original language name
Polyfunctional beta-Dicarbonyl Compounds by Michael Addition Reactions of Ester Enolates to alpha-Benzylidene and alpha-Alkylidene-beta-dicarbonyl Compounds
Original language description
The scope and stereoselectivity of the Michael addition of ester enolates to a-benzylidene and a-alkylidene beta-dicarbonyl compounds was studied. Most substrates reacted in good to excellent yields. Michael acceptors bearing carboxylic functionalities reacted directly in the beta-position, whereas aldol and Michael addition competed with unsaturated ketones. The diastereoselectivity of the process is dependent on the substitution pattern of the Michael acceptor and the geometry of the enolate. (Z)-Enolates add to unsaturated malonates or dibenzoylmethane derivatives with good anti-selectivity, whereas (E)-enolates afforded the syn-diastereomers predominately. Unsaturated nitriles and Meldrum's acid derivatives reacted with low diastereoselectivity. Astereochemical model is proposed that accounts for all experimental results and allows the stereochemical outcome to be predicted.
Czech name
—
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
—

Project
<a href="/en/project/GA203%2F09%2F1936" target="_blank" >GA203/09/1936: Unprecedented Domino Processes Involving the Directed Application of Anionic, Transition Metal-Catalyzed, Radical and Carbocationic Reaction Steps</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)<br>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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