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A Catalytic Asymmetric Ring‐Expansion Reaction of Isatins and α‐Alkyl‐α‐Diazoesters: Highly Efficient Synthesis of Functionalized 2‐Quinolone Derivatives
Author(s) -
Li Wei,
Liu Xiaohua,
Hao Xiaoyu,
Cai Yunfei,
Lin Lili,
Feng Xiaoming
Publication year - 2012
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.201204594
Subject(s) - stereocenter , catalysis , chemistry , ring (chemistry) , ligand (biochemistry) , selectivity , combinatorial chemistry , quinolone , alkyl , medicinal chemistry , stereochemistry , enantioselective synthesis , organic chemistry , receptor , biochemistry , antibiotics
Asymmetric expansion : A catalytic asymmetric ring‐expansion reaction of the title compounds occurs in the presence of a Sc(OTf) 3 catalyst bearing an N , N ′‐dioxide‐based ligand. Highly functionalized 2‐quinolone derivatives containing a chiral C4‐quaternary stereocenter were obtained in high yields and high levels of selectivity under mild reaction conditions (see scheme; Tf=trifluoromethanesulfonyl).