A Catalytic Asymmetric Ring‐Expansion Reaction of Isatins and α‐Alkyl‐α‐Diazoesters: Highly Efficient Synthesis of Functionalized 2‐Quinolone Derivatives | Zendy

Li Wei | Zendy; Liu Xiaohua | Zendy; Hao Xiaoyu | Zendy; Cai Yunfei | Zendy; Lin Lili | Zendy; Feng Xiaoming | Zendy

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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).

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