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Asymmetric Synthesis of Spiropyrazolones by Rhodium‐Catalyzed C(sp 2 )−H Functionalization/Annulation Reactions
Author(s) -
Zheng Jun,
Wang ShaoBo,
Zheng Chao,
You ShuLi
Publication year - 2017
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.201700021
Subject(s) - annulation , stereocenter , rhodium , pyrazolones , chemistry , catalysis , enantioselective synthesis , surface modification , aryl , yield (engineering) , ring (chemistry) , combinatorial chemistry , medicinal chemistry , organic chemistry , materials science , alkyl , metallurgy
Rhodium‐catalyzed C(sp 2 )−H functionalization reactions of 4‐aryl‐5‐pyrazolones followed by [3+2] annulation reactions with alkynes provide rapid access to highly enantioenriched five‐membered‐ring 4‐spiro‐5‐pyrazolones. The use of a chiral SCpRh catalyst enabled the synthesis of a large range of spiropyrazolones with all‐carbon quaternary stereogenic centers in up to 99 % yield and 98 % ee from readily available substrates.