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

Hongzhou Yang; Qingqing Wang; Yuan Luo; Ling Ye; Xinying Li; Feng Chen; Zhigang Zhao; Xuefeng Li

doi:10.1039/d0ob00004c

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

Org Biomol Chem. 2020 Feb 26;18(8):1607-1611. doi: 10.1039/d0ob00004c.

Authors

Hongzhou Yang¹, Qingqing Wang¹, Yuan Luo¹, Ling Ye², Xinying Li¹, Feng Chen¹, Zhigang Zhao¹, Xuefeng Li¹

Affiliations

¹ College of Chemistry and Environment Protection Engineering, Southwest Minzu University, Chengdu 610041, China. lixuefeng@swun.edu.cn.
² Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China.

PMID: 32030393
DOI: 10.1039/d0ob00004c

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.

Publication types

Research Support, Non-U.S. Gov't