Asymmetric Diels–Alder Cycloadditions of Trifluoromethylated Dienophiles Under Trienamine Catalysis |
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| Authors: | Xin Yuan Dr. Shan‐Jun Zhang Dr. Wei Du Prof. Dr. Ying‐Chun Chen |
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| Affiliation: | 1. Key Laboratory of Drug-Targeting, and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University, Chengdu, P. R. China;2. College of Pharmacy, Third Military Medical University, Chongqing, P. R. China |
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| 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 NaBH3CN 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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| Keywords: | asymmetric catalysis cycloaddition Diels– Alder reaction octahydroisoquinoline trifluoromethyl |
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