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  • Title: Asymmetric Diels-Alder Cycloadditions of Trifluoromethylated Dienophiles Under Trienamine Catalysis.
    Author: Yuan X, Zhang SJ, Du W, Chen YC.
    Journal: Chemistry; 2016 Jul 25; 22(31):11048-52. PubMed ID: 27305465.
    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.
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