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Asymmetric Dearomative Fluorination of 2‐Naphthols with a Dicarboxylate Phase‐Transfer Catalyst
Author(s) -
Egami Hiromichi,
Rouno Taiki,
Niwa Tomoki,
Masuda Kousuke,
Yamashita Kenji,
Hamashima Yoshitaka
Publication year - 2020
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.202005367
Subject(s) - selectfluor , enantioselective synthesis , catalysis , chemistry , phase (matter) , molecule , combinatorial chemistry , organic chemistry , stereochemistry
A linked dicarboxylate phase‐transfer catalyst enables smooth asymmetric dearomative fluorination of 2‐naphthols with Selectfluor under mild conditions to give the corresponding 1‐fluoronaphthalenone derivatives in a highly enantioselective manner. This reaction, which is compatible with a range of functional groups, is the first example of catalytic asymmetric fluorination of 2‐naphthols, and is expected to be useful in the synthesis of bioactive molecules.