Jump to main content
Jump to site search


Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Author affiliations

Abstract

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.

Graphical abstract: Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

Back to tab navigation

Supplementary files

Publication details

The article was received on 16 Apr 2019, accepted on 07 May 2019 and first published on 07 May 2019


Article type: Communication
DOI: 10.1039/C9OB00884E
Org. Biomol. Chem., 2019, Advance Article

  •   Request permissions

    Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

    J. Otevrel, D. Svestka and P. Bobal, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00884E

Search articles by author

Spotlight

Advertisements