Asymmetric Diels-Alder Cycloadditions of Trifluoromethylated Dienophiles Under Trienamine Catalysis.
β-Trifluoromethyl (CF3 ) enones were proved to act as good dienophiles in asymmetric normal-electron-demand Diels-Alder cycloadditions with 2,4-dienals under trienamine catalysis with a chiral secondary amine. The sequential reductive amination transformations with benzylamine produced cis- and trans-fused chiral trifluoromethylated octahydroisoquinolines in a diastereodivergent manner by using NaBH(OAc)3 and NaBH3 CN as the reductants, respectively. Moreover, other types of activated alkenes that bear a CF3 group have also been successfully utilized to construct a diverse range of chiral cyclic frameworks in high stereoselectivity.
Key Laboratory of Drug-Targeting, and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.
Xin
X
Yuan
Key Laboratory of Drug-Targeting, and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.
Shan-Jun
SJ
Zhang
Key Laboratory of Drug-Targeting, and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China.
Wei
W
Du
Key Laboratory of Drug-Targeting, and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, 610041, P. R. China. ycchen@scu.edu.cn.|College of Pharmacy, Third Military Medical University, Chongqing, 400038, P. R. China. ycchen@scu.edu.cn.
Ying-Chun
YC
Chen
Diels-Alder reaction; asymmetric catalysis; cycloaddition; octahydroisoquinoline; trifluoromethyl