Highly Enantioselective Organocatalytic Formation of Functionalized Cyclopentane Derivatives via Tandem Conjugate Addition/alpha-Alkylation of Enals

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F12%3A10127434" target="_blank" >RIV/00216208:11310/12:10127434 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201200334" target="_blank" >http://dx.doi.org/10.1002/ejoc.201200334</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201200334" target="_blank" >10.1002/ejoc.201200334</a>

Result language
angličtina
Original language name
Highly Enantioselective Organocatalytic Formation of Functionalized Cyclopentane Derivatives via Tandem Conjugate Addition/alpha-Alkylation of Enals
Original language description
An enantioselective tandem reaction between dialkyl 2-haloethylmalonates and aromatic enals catalyzed by secondary amine catalysts is described. The reaction proceeds through a Michael/alpha-alkylation reaction sequence to afford the final 1,1,2,3-tetrasubstituted cyclopentanes in good yields (up to 75%) with high diastereoselectivity and enantioselectivity (up to 20:1dr and 93%ee). Moreover, the Michael/alpha-alkylation reaction also proceeds with a low catalyst loading (5 mol-%) with only a slight influence on selectivity and Oand N-alkylation products were not observed.
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
Z - Vyzkumny zamer (s odkazem do CEZ)<br>S - Specificky vyzkum na vysokych skolach<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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