Recoverable polystyrene-supported catalysts for Sharpless allylic alcohols epoxidations

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216275%3A25310%2F19%3A39914455" target="_blank" >RIV/00216275:25310/19:39914455 - isvavai.cz</a>
Result on the web
<a href="https://www.sciencedirect.com/science/article/pii/S1381514818309738" target="_blank" >https://www.sciencedirect.com/science/article/pii/S1381514818309738</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1016/j.reactfunctpolym.2019.01.009" target="_blank" >10.1016/j.reactfunctpolym.2019.01.009</a>

Result language
angličtina
Original language name
Recoverable polystyrene-supported catalysts for Sharpless allylic alcohols epoxidations
Original language description
n this work, new heterogeneous catalysts intended for enantioselective Sharpless epoxidation were prepared. The catalysts are based on Ti(IV) complexes of cross-linked swellable spherical copolymer beads of styrene with ethyl-(4-vinylbenzyl)-L-tartrate, or with ethyl-(2R,3R)-2,3-dihydroxy-4-oxo-5-(4-vinylphenyl)pentanoate. These catalysts were tested in epoxidation of cinnamyl alcohols. High conversion (up to 99%) and high enantioselectivity (up to 99% ee) were achieved in the case of catalysts based on copolymers of styrene with ethyl-(4-vinylbenzyl)-L-tartrate (5, 20, 50%). Unfortunately, the copolymers lost their enantioselectivity due to the leaching of L-tartrate, caused by alcoholysis of ester bond. This problem has been overcome by replacing the ester bond by a stable keto bond. The prepared catalyst based on the copolymer of styrene with ethyl-(2R,3R)-2,3-dihydroxy-4-oxo-5-(4-vinylphenyl)pentanoate (20%) achieved a similarly high conversion and enantioselectivity as in the previous case (up to 99%, up to 99% ee) and was successfully recycled.
Czech name
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Czech description
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Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA17-08499S" target="_blank" >GA17-08499S: Recyclable Catalysts for Sustainable Technologies of Advanced Organic Intermediates</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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