Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via organocatalytic cascade Michael/aldol reaction
2020
An enantioselective (92-99% ee) Michael/aldol cascade reaction between 4,4,4-trifluoroacetoacetates and α,β-unsaturated enones was established in the presence of cinchona alkaloid-based primary amines. Various β-CF3-cyclohexanones were constructed in high yields (81-99%) as a couple of separable diastereomers. This tandem reaction was sensitive to acidic co-catalyst, with a Michael/aldol condensation process favorably occurring to generate β-CF3-cyclohexenones (42-69% yield, 84-96% ee) in the presence of trifluoroacetic acid.
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