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Asymmetric Arylative Dearomatization of β‐Naphthols Catalyzed by a Chiral Phosphoric Acid
Author(s) -
Li XiaoQiang,
Yang Hui,
Wang JiaoJiao,
Gou BoBo,
Chen Jie,
Zhou Ling
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701015
Subject(s) - aromatization , enantioselective synthesis , phosphoric acid , catalysis , yield (engineering) , chemistry , substrate (aquarium) , domino , organic chemistry , reactivity (psychology) , combinatorial chemistry , materials science , medicine , oceanography , alternative medicine , pathology , metallurgy , geology
An enantioselective arylative dearomatization reaction of β‐naphthols with quinone monoimides has been developed for the first time using a chiral phosphoric acid as the catalyst, the desired enantioenriched cyclohexadienones were prepared with excellent yields and enantioselectivities by a domino Michael addition and aromatization process (up to 99 % yield, up to 98 % ee ). This process is operationally simple and readily scaled up, as well as a broad substrate scope which includes 1‐substituted‐2‐naphthols with/without 3‐substituents. Furthermore, this organocatalytic procedure allows the lowering of catalyst loading to 0.5 mol % without considerable loss in reactivity and enantioselectivity.