AI Article Synopsis
- This study highlights a new method for a specific type of chemical reaction called enantioselective Michael addition, using a piperazine-thiourea catalyst.
- The process effectively combines alpha-cyanoketones with alpha,beta-unsaturated trifluoromethyl ketones, yielding alpha-trifluoromethyldihydropyrans in high amounts and with very high enantiomeric excess (up to 95%).
- Additionally, the research showcases a practical way to further transform the resulting chiral product, enhancing its utility in applications.
Article Abstract
The first enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trifluoromethyl ketones using a novel piperazine-thiourea catalyst was described. The resulting alpha-trifluoromethyldihydropyrans were obtained in high yields and with up to 95% ee within a short reaction time. A useful transformation of the chiral adduct was also illustrated.
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| http://dx.doi.org/10.1039/b915210e | DOI Listing |
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Highly enantio- and diastereoselective synthesis of alpha-trifluoromethyldihydropyrans using a novel bifunctional piperazine-thiourea catalyst.
Chem Commun (Camb)
December 2009
Key Laboratory of Organofluorine Chemistry and Key Laboratory of Modern Synthetic Organic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai, 200032, China.
The first enantioselective Michael addition of alpha-cyanoketones to alpha,beta-unsaturated trifluoromethyl ketones using a novel piperazine-thiourea catalyst was described. The resulting alpha-trifluoromethyldihydropyrans were obtained in high yields and with up to 95% ee within a short reaction time. A useful transformation of the chiral adduct was also illustrated.
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