Asymmetric Diels-Alder Cycloadditions of Trifluoromethylated Dienophiles Under Trienamine Catalysis

Xin Yuan; Shan-Jun Zhang; Wei Du; Ying-Chun Chen

doi:10.1002/chem.201600989

Asymmetric Diels-Alder Cycloadditions of Trifluoromethylated Dienophiles Under Trienamine Catalysis

Chemistry. 2016 Jul 25;22(31):11048-52. doi: 10.1002/chem.201600989. Epub 2016 Jun 15.

Authors

Xin Yuan¹, Shan-Jun Zhang¹, Wei Du¹, Ying-Chun Chen^{2

3}

Affiliations

¹ 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.
² 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.
³ College of Pharmacy, Third Military Medical University, Chongqing, 400038, P. R. China. ycchen@scu.edu.cn.

PMID: 27305465
DOI: 10.1002/chem.201600989

Abstract

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.

Keywords: Diels-Alder reaction; asymmetric catalysis; cycloaddition; octahydroisoquinoline; trifluoromethyl.