Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F62157124%3A16370%2F19%3A43877860" target="_blank" >RIV/62157124:16370/19:43877860 - isvavai.cz</a>

Výsledek na webu

<a href="https://doi.org/10.1039/c9ob00884e" target="_blank" >https://doi.org/10.1039/c9ob00884e</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1039/c9ob00884e" target="_blank" >10.1039/c9ob00884e</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Popis výsledku v původním jazyce

We have developed a catalytic system based on bianthrylbis (thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3 : 2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.

Název v anglickém jazyce

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Popis výsledku anglicky

We have developed a catalytic system based on bianthrylbis (thiourea) for the asymmetric Henry reaction of fluoroketones and nitroalkanes that resulted from the screening of a library containing 31 chiral non-racemic organocatalysts. The corresponding adducts were isolated in up to 6 times shorter reaction time in comparison with the previously published organocatalysts. High levels of stereocontrol have been generally observed, with measured product enantiomeric excesses up to 97% and diastereomeric ratio 3 : 2 (anti/syn). The above-mentioned catalysts have been successfully applied to the total asymmetric synthesis of CF3-tethered (S)-halostachines, which has proved that this method constitutes an easy entry to similar enantiopure compounds.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

30107 - Medicinal chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2019

Kód důvěrnosti údajů

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

Název periodika

Organic &amp; biomolecular chemistry

ISSN

1477-0520

e-ISSN

—

Svazek periodika

17

Číslo periodika v rámci svazku

21

Stát vydavatele periodika

GB - Spojené království Velké Británie a Severního Irska

Počet stran výsledku

5

Strana od-do

5244-5248

Kód UT WoS článku

000471015200006

EID výsledku v databázi Scopus

2-s2.0-85066445477