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Umpolung of Imines Enables Catalytic Asymmetric Regio‐reversed [3+2] Cycloadditions of Iminoesters with Nitroolefins
Author(s) -
Feng Bin,
Lu LiangQiu,
Chen JiaRong,
Feng Guoqiang,
He BinQing,
Lu Bin,
Xiao WenJing
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.201802492
Subject(s) - umpolung , catalysis , cycloaddition , chemistry , regioselectivity , aryl , combinatorial chemistry , enantioselective synthesis , organic chemistry , stereochemistry , alkyl , nucleophile
A copper‐catalyzed regio‐reversed asymmetric [3+2] cycloaddition of iminoesters with nitroolefins is disclosed for the first time. This method enables the facile synthesis of polysubstituted chiral pyrrolidines bearing at least one chiral quaternary center in high yields with excellent regio‐, diastereo‐, and enantioselectivity. The application of chiral P,S ligands and the unique effect of α‐aryl groups on the iminoesters are key to the success of this method. The practicality and versatility of the reaction are also demonstrated.