Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F14%3A10271744" target="_blank" >RIV/00216208:11310/14:10271744 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1021/jo4022106" target="_blank" >http://dx.doi.org/10.1021/jo4022106</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/jo4022106" target="_blank" >10.1021/jo4022106</a>

Result language
angličtina
Original language name
Organocatalytic Preparation of Substituted Cyclopentanes: A Mechanistic Study
Original language description
The reaction mechanism of a tandem conjugate addition/alpha-alkylation of enals leading to functionalized cyclopentanes catalyzed by O-trimethylsilyldiphenylprolinol was investigated by mass spectrometry, NMR spectroscopy, and DFT calculations. We have shown that the high stereoselectivity of the reaction depends on the energy discrimination between the two stereoisomers formed by the condensation of the alpha,beta-unsaturated aldehyde (cinnamaldehyde) and the catalyst. The stereoselectivity of this step depends on the solvent used. The experimental activation barriers were determined to be E-a = 25 +/- 7 kJ mol(-1) (Arrhenius equation), Delta H-double dagger = 23 +/- 7 kJ mol(-1) and Delta G(double dagger) = 101 +/- 9 kJ mol(-1) (Eyring equation).
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
2014
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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