Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Result code in 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>

Result on the web

<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>

Result language

angličtina

Original language name

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

30107 - Medicinal chemistry

Project

—

Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2019

Confidentiality

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

Name of the periodical

Organic &amp; biomolecular chemistry

ISSN

1477-0520

e-ISSN

—

Volume of the periodical

17

Issue of the periodical within the volume

21

Country of publishing house

GB - UNITED KINGDOM

Number of pages

5

Pages from-to

5244-5248

UT code for WoS article

000471015200006

EID of the result in the Scopus database

2-s2.0-85066445477