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A Copper Catalyst with a Cinchona‐Alkaloid‐Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes
Author(s) -
Li XiTao,
Gu QiangShuai,
Dong XiaoYang,
Meng Xiang,
Liu XinYuan
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.201804315
Subject(s) - stereocenter , chemistry , sulfonamide , cinchona , reagent , oxime , catalysis , enantioselective synthesis , yield (engineering) , copper , alkyl , combinatorial chemistry , ligand (biochemistry) , organic chemistry , materials science , biochemistry , receptor , metallurgy
A copper‐catalyzed asymmetric radical oxytrifluoromethylation of alkenyl oxime and Togni's reagent has been successfully developed, thereby providing straightforward access to CF 3 ‐containing isoxazolines bearing α‐tertiary stereocenters with excellent yield and enantioselectivity. The key to success is the rational design of cinchona‐alkaloid‐based sulfonamides as neutral/anionic hybrid ligands to effectively control the stereochemistry in copper‐catalyzed reactions involving free alkyl radical species. The utility of this method is illustrated by efficient transformation of the products into useful chiral CF 3 ‐containing 1,3‐aminoalcohols.