Issue 21, 2019

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

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

Supplementary files

Article information

Article type
Communication
Submitted
16 Apr 2019
Accepted
07 May 2019
First published
07 May 2019

Org. Biomol. Chem., 2019,17, 5244-5248

Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones

J. Otevrel, D. Svestka and P. Bobal, Org. Biomol. Chem., 2019, 17, 5244 DOI: 10.1039/C9OB00884E

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