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Palladium‐Catalyzed Cascade sp 2 C−H Functionalization/Intramolecular Asymmetric Allylation: From Aryl Ureas and 1,3‐Dienes to Chiral Indolines
Author(s) -
Chen ShuSen,
Wu MinSong,
Han ZhiYong
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.201702745
Subject(s) - chemistry , intramolecular force , sulfoxide , aryl , chiral ligand , palladium , indoline , catalysis , oxazoline , cascade reaction , surface modification , ligand (biochemistry) , combinatorial chemistry , medicinal chemistry , cascade , enantioselective synthesis , stereochemistry , organic chemistry , biochemistry , alkyl , receptor , chromatography
A chiral Pd II ‐catalyzed cascade sp 2 C−H functionalization/intramolecular asymmetric allylation reaction is reported. A new chiral sulfoxide–oxazoline (SOX) ligand bearing single chiral center on the sulfur was identified as the optimal ligand for the reaction, being efficient both in the C−H cleavage step and the stereocontrol of the allylation step. The broad scope of this method with respect to aryl ureas and 1,3‐dienes enables the rapid construction of valuable chiral indoline derivatives with high yields and enantioselectivities (up to 99 % yield, up to 95:5 e.r.).