3 years ago

Anilines as C-Nucleophiles in Ir-Catalyzed Intramolecular Asymmetric Allylic Substitution Reactions

Anilines as C-Nucleophiles in Ir-Catalyzed Intramolecular Asymmetric Allylic Substitution Reactions
Shu-Li You, Qing Gu, Xin-Yan Wu, Zheng-Le Zhao
Anilines generally act as N-nucleophiles in transition-metal-catalyzed allylic substitution reactions. In this paper, a highly enantioselective intramolecular Friedel–Crafts-type allylic alkylation of aniline derivatives was realized by using an iridium catalyst derived from [Ir(cod)Cl]2 and (Ra)-BHPphos. Various tetrahydroisoquinilin-5-amines were obtained in moderate to good yields, excellent enantioselectivity and regioselectivity under mild reaction conditions. BHPphos=N-benzhydryl-N-phenyldinaphthophosphoramidite. Switch from N to C: Anilines generally act as N-nucleophiles in transition-metal-catalyzed allylic substitution reactions. In this paper, a highly enantioselective intramolecular Friedel–Crafts-type allylic alkylation of aniline derivatives was realized by using an iridium catalyst derived from [Ir(cod)Cl]2 and (Ra)-N-benzhydryl-N-phenyldinaphthophosphoramidite ((Ra)-BHPphos).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/asia.201701192

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