Preparations of spherical nanoparticles of chiral Cinchona alkaloid-based bridged silsesquioxanes and their use in heterogeneous catalysis of enantioselective reactions

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F24%3A00584832" target="_blank" >RIV/67985858:_____/24:00584832 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/46747885:24620/24:00012139 RIV/60461373:22310/24:43928778 RIV/60461373:22340/24:43928778

Výsledek na webu

<a href="https://pubs.rsc.org/en/content/articlepdf/2024/nr/d3nr06234a" target="_blank" >https://pubs.rsc.org/en/content/articlepdf/2024/nr/d3nr06234a</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/d3nr06234a" target="_blank" >10.1039/d3nr06234a</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Preparations of spherical nanoparticles of chiral Cinchona alkaloid-based bridged silsesquioxanes and their use in heterogeneous catalysis of enantioselective reactions

Popis výsledku v původním jazyce

Two spherical nanoparticulate materials were prepared by base-catalyzed sol-gel hydrolysis/self-condensation of the bis-Cinchona alkaloid-phthalazine-based bridged bis(triethoxysilanes). For the purpose of comparing the catalytic properties, two compact materials were also prepared from the same precursors using a fluoride-catalyzed sol-gel process. All materials were characterized by SEM, TEM, solid-state( 29)Si NMR and C-13 NMR, TGA, and FTIR. The prepared silsesquioxane-based materials were studied as potential heterogeneous catalysts for selected enantioselective reactions. The spherical material with regularly incorporated bis-quinine-phthalazine chiral units exhibited good to excellent enantioselectivities in osmium-catalyzed dihydroxylations of alkenes. Enantioselectivities observed in dihydroxylations of aromatic trans-alkenes were as excellent as those observed with the homogeneous catalyst (DHQ)(2)-PHAL. One compact and one nanoparticulate material was successfully recycled and reused five times without loss of enantioselectivity. Furthermore, both quinine-based and cinchonine-based materials were tested as heterogeneous organocatalysts for chlorolactonization of 4-arylpent-4-enoic acids. The materials showed only moderate enantioselectivities, however, these are the first heterogeneous catalysts for enantioselective chlorolactonization published so far.

Název v anglickém jazyce

Preparations of spherical nanoparticles of chiral Cinchona alkaloid-based bridged silsesquioxanes and their use in heterogeneous catalysis of enantioselective reactions

Popis výsledku anglicky

Two spherical nanoparticulate materials were prepared by base-catalyzed sol-gel hydrolysis/self-condensation of the bis-Cinchona alkaloid-phthalazine-based bridged bis(triethoxysilanes). For the purpose of comparing the catalytic properties, two compact materials were also prepared from the same precursors using a fluoride-catalyzed sol-gel process. All materials were characterized by SEM, TEM, solid-state( 29)Si NMR and C-13 NMR, TGA, and FTIR. The prepared silsesquioxane-based materials were studied as potential heterogeneous catalysts for selected enantioselective reactions. The spherical material with regularly incorporated bis-quinine-phthalazine chiral units exhibited good to excellent enantioselectivities in osmium-catalyzed dihydroxylations of alkenes. Enantioselectivities observed in dihydroxylations of aromatic trans-alkenes were as excellent as those observed with the homogeneous catalyst (DHQ)(2)-PHAL. One compact and one nanoparticulate material was successfully recycled and reused five times without loss of enantioselectivity. Furthermore, both quinine-based and cinchonine-based materials were tested as heterogeneous organocatalysts for chlorolactonization of 4-arylpent-4-enoic acids. The materials showed only moderate enantioselectivities, however, these are the first heterogeneous catalysts for enantioselective chlorolactonization published so far.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2024

Kód důvěrnosti údajů

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

Název periodika

Nanoscale

ISSN

2040-3364

e-ISSN

2040-3372

Svazek periodika

16

Číslo periodika v rámci svazku

13

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

12

Strana od-do

6696-6707

Kód UT WoS článku

001185494600001

EID výsledku v databázi Scopus

2-s2.0-85187993432