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Asymmetric Synthesis of Fluorinated Flavanone Derivatives by an Organocatalytic Tandem Intramolecular Oxa‐Michael Addition/Electrophilic Fluorination Reaction by Using Bifunctional Cinchona Alkaloids
Author(s) -
Wang HaiFeng,
Cui HaiFeng,
Chai Zhuo,
Li Peng,
Zheng ChangWu,
Yang YingQuan,
Zhao Gang
Publication year - 2009
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.200902303
Subject(s) - bifunctional , chemistry , intramolecular force , electrophile , flavanone , michael reaction , cascade reaction , tandem , cinchona alkaloids , trifluoromethyl , organocatalysis , derivative (finance) , organic chemistry , stereochemistry , combinatorial chemistry , enantioselective synthesis , catalysis , materials science , alkyl , flavonoid , financial economics , economics , composite material , antioxidant
A bifunctional quinidine derivative , containing a trifluoromethyl group, was found to catalyze a tandem intramolecular oxa‐Michael addition/electrophilic fluorination reaction of activated α,β‐unsaturated ketones (see scheme). A series of chiral fluorinated flavanone derivatives were obtained in excellent yields and with high enantioselectivities.