Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 17, Issue 21, Pages 5244-5248Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c9ob00884e
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Funding
- IGA UVPS Brno [301/2019/FaF, 315/2019/FaF]
- MEYS CR [LM2015043]
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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.
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