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Enantioselective synthesis of trifluoromethyl substituted cyclohexanones via an organocatalytic cascade Michael/aldol reaction. 2020
Hongzhou Yang, and
Qingqing Wang, and
Yuan Luo, and
Ling Ye, and
Xinying Li, and
Feng Chen, and
Zhigang Zhao, and
Xuefeng Li
College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China. lixuefeng@swun.edu.cn.
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.
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