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Catalytic Asymmetric Dearomatization of Indolyl Dihydropyridines through an Enamine Isomerization/Spirocyclization/Transfer Hydrogenation Sequence
Author(s) -
Xia ZiLei,
Zheng Chao,
Wang ShouGuo,
You ShuLi
Publication year - 2018
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.201712435
Subject(s) - isomerization , enamine , chemistry , catalysis , transfer hydrogenation , sequence (biology) , combinatorial chemistry , organocatalysis , phosphoric acid , enantioselective synthesis , organic chemistry , biochemistry , ruthenium
A highly efficient synthesis of enantioenriched spiroindolines by catalytic asymmetric dearomatization of indolyl dihydropyridines through a chiral phosphoric acid catalyzed enamine isomerization/spirocyclization/transfer hydrogenation sequence has been developed. This reaction proceeds under mild reaction conditions, affording novel spiroindolines in good yields (up to 88 %) with excellent enantioselectivity (up to 97 % ee ). DFT calculations provide insights into the reaction mechanism as well as the origin of stereochemistry.