Polystyrene supported benzoylthiourea-pyrrolidine organocatalyst for the enantioselective Michael addition

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F16%3A39901632" target="_blank" >RIV/00216275:25310/16:39901632 - isvavai.cz</a>
Result on the web
<a href="http://dx.doi.org/10.1016/j.tetasy.2016.06.015" target="_blank" >http://dx.doi.org/10.1016/j.tetasy.2016.06.015</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.tetasy.2016.06.015" target="_blank" >10.1016/j.tetasy.2016.06.015</a>

Result language
angličtina
Original language name
Polystyrene supported benzoylthiourea-pyrrolidine organocatalyst for the enantioselective Michael addition
Original language description
Herein the preparation of a swellable pearl-like copolymer of styrene with anchored (S)-1-benzoyl-3-(pyrrolidine-2-ylmethyl)thiourea (20-600 mu m) and its application as a recyclable organocatalyst for the Michael addition of ketones to functionalized beta-nitrostyrenes is described. The rate of the reaction taking place in the matrix of the swellable polymeric catalyst was comparable with the reaction rate in homogeneous medium. The corresponding functionalized 4-nitroketones were formed quantitatively with the enantiomeric excesses up to 98% ee. After a fivefold recycling of the catalyst, no decrease in the yield was detected, but the enantioselectivity was slightly lowered (95 -> 88% ee).
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
<a href="/en/project/GA14-00925S" target="_blank" >GA14-00925S: Immobilized Enantioselective Catalysts</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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