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Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction

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Abstract

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-catalysts, 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.

Graphical abstract: Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction

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Article information


Submitted
02 Jan 2020
Accepted
03 Feb 2020
First published
03 Feb 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction

H. Yang, Q. Wang, Y. Luo, L. Ye, X. Li, F. Chen, Z. Zhao and X. Li, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00004C

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