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Enantioselective Synthesis of Isoxazolines Enabled by Palladium‐Catalyzed Carboetherification of Alkenyl Oximes
Author(s) -
Wang Lei,
Zhang Kenan,
Wang Yuzhuo,
Li Wenbo,
Chen Mingjie,
Zhang Junliang
Publication year - 2020
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.201912408
Subject(s) - enantioselective synthesis , chemistry , steric effects , substrate (aquarium) , aryl , catalysis , functional group , palladium , combinatorial chemistry , ligand (biochemistry) , halide , organic chemistry , reaction conditions , alkyl , biochemistry , oceanography , polymer , receptor , geology
Abstract Reported here is a highly efficient Pd/Xiang‐Phos catalyzed enantioselective carboetherification of alkenyl oximes with either aryl or alkenyl halides, delivering various chiral 3,5‐disubstituted and 3,5,5‐trisubstituted isoxazolines in good yields with up to 97 % ee . The sterically bulky and electron‐rich ( S , R s)‐ NMe‐X2 ligand is responsible for the excellent reactivities and enantioselectivities. The salient features of this transformation include mild reaction conditions, general substrate scope, good functional‐group tolerance, good yields, high enantioselectivities, easy scale‐up, and application in the late‐stage modification of bioactive compounds. The obtained products can be readily transformed into useful chiral 1,3‐aminoalcohols.