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Enantioselective Dearomatization of Naphthol Derivatives with Allylic Alcohols by Cooperative Iridium and Brønsted Acid Catalysis
Author(s) -
Shen Dan,
Chen Qiliang,
Yan Peipei,
Zeng Xiaofei,
Zhong Guofu
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201609693
Subject(s) - enantioselective synthesis , allylic rearrangement , iridium , chemistry , catalysis , enantiomer , phosphoric acid , combinatorial chemistry , organic chemistry
The combination of a transition‐metal catalyst and organocatalyst was designed to achieve a highly enantioselective system for the allylic dearomatization reaction of naphthols with racemic secondary allylic alcohols. The desired β‐naphthalenones, bearing an all‐carbon quaternary center, were obtained in good yields with high chemo‐ and enantioselectivities. The cooperative catalytic system, involving a chiral iridium complex and phosphoric acid, provided measurable improvements in yields, and chemo‐ and enantioselectivities relative to single‐catalyst systems. Control experiments indicated that the chiral iridium complex functions as a key species in the control of the absolute configuration, thus enabling the formation of both β‐naphthalenone enantiomers by simply employing opposite enantiomeric ligands.