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Catalytic Asymmetric Homologation of α‐Ketoesters with α‐Diazoesters: Synthesis of Succinate Derivatives with Chiral Quaternary Centers
Author(s) -
Li Wei,
Liu Xiaohua,
Tan Fei,
Hao Xiaoyu,
Zheng Jianfeng,
Lin Lili,
Feng Xiaoming
Publication year - 2013
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.201305478
Subject(s) - stereocenter , catalysis , yield (engineering) , alkyl , chemistry , aryl , combinatorial chemistry , enantioselective synthesis , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy
Y not? In the presence of the L /Y(OTf) 3 catalyst, the first catalytic asymmetric homologation of α‐ketoesters with α‐alkyl‐α‐diazoesters through either a 1,2‐aryl or 1,2‐alkyl shift was accomplished. Highly functionalized succinate derivatives containing a quaternary stereocenter were obtained in excellent yield and enantioselectivity under mild reaction conditions. Tf=trifluoromethanesulfonyl.