Recoverable polystyrene-supported catalysts for Sharpless allylic alcohols epoxidations

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

Recoverable polystyrene-supported catalysts for Sharpless allylic alcohols epoxidations

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Recoverable polystyrene-supported catalysts for Sharpless allylic alcohols epoxidations

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

<a href="/cs/project/GA17-08499S" target="_blank" >GA17-08499S: Recyklovatelné katalyzátory pro udržitelné technologie pokročilých organických intermediátů</a><br>

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2019

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Reactive and Functional Polymers

ISSN

1381-5148

e-ISSN

—

Svazek periodika

137

Číslo periodika v rámci svazku

April

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

10

Strana od-do

"123–132"

Kód UT WoS článku

000463123200014

EID výsledku v databázi Scopus

2-s2.0-85061966450