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Anilines as C‐Nucleophiles in Ir‐Catalyzed Intramolecular Asymmetric Allylic Substitution Reactions
Author(s) -
Zhao ZhengLe,
Gu Qing,
Wu XinYan,
You ShuLi
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201701192
Subject(s) - allylic rearrangement , intramolecular force , regioselectivity , chemistry , enantioselective synthesis , nucleophile , iridium , catalysis , substitution reaction , aniline , medicinal chemistry , nucleophilic substitution , tsuji–trost reaction , organic chemistry
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 ( R a )‐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.
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