Publication details
Bianthryl-based organocatalysts for the asymmetric Henry reaction of fluoroketones
| Authors | |
|---|---|
| Year of publication | 2019 |
| Type | Article in Periodical |
| Magazine / Source | ORGANIC & BIOMOLECULAR CHEMISTRY |
| MU Faculty or unit | |
| Citation | |
| web | https://pubs.rsc.org/en/content/articlelanding/2019/OB/C9OB00884E |
| Doi | https://doi.org/10.1039/c9ob00884e |
| Keywords | CATALYSTS; EFFICIENT; AMINES |
| 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. |