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Asymmetric Synthesis of α,α‐Disubstituted Allylic Amines through Palladium‐Catalyzed Allylic Substitution
Author(s) -
Guo Wusheng,
Cai Aijie,
Xie Jianing,
Kleij Arjan W.
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.201705825
Subject(s) - allylic rearrangement , palladium , chemistry , amine gas treating , catalysis , reagent , substitution reaction , asymmetric induction , enantiomer , aryl , enantioselective synthesis , combinatorial chemistry , substitution (logic) , alkyl , medicinal chemistry , organic chemistry , computer science , programming language
The first asymmetric synthesis of important α,α‐disubstituted N‐alkyl allyl amine scaffolds through allylic substitution is reported. This approach is based on palladium catalysis and features ample scope with respect to both the allylic precursor and amine reagent, and high asymmetric induction with enantiomeric ratios (e.r.) up to 98.5:1.5. The use of less‐reactive anilines is also feasible, providing enantioenriched α,α‐disubstituted N‐aryl allylic amines.