A Copper Catalyst with a Cinchona‐Alkaloid‐Based Sulfonamide Ligand for Asymmetric Radical Oxytrifluoromethylation of Alkenyl Oximes

A copper‐catalyzed asymmetric radical oxytrifluoromethylation of alkenyl oxime and Togni's reagent has been successfully developed, thereby providing straightforward access to CF3‐containing isoxazolines bearing α‐tertiary stereocenters with excellent yield and enantioselectivity. The key to su...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2018-06, Vol.57 (26), p.7668-7672
Main Authors: Li, Xi‐Tao, Gu, Qiang‐Shuai, Dong, Xiao‐Yang, Meng, Xiang, Liu, Xin‐Yuan
Format: Article
Language:English
Subjects:
alkenyl oximes
Antibiotics
asymmetric catalysis
CF3-containing isoxazolines
Chemical reactions
Copper
Enantiomers
Ligands
Oximes
radical reactions
Reagents
Stereochemistry
Sulfonamides
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Summary:A copper‐catalyzed asymmetric radical oxytrifluoromethylation of alkenyl oxime and Togni's reagent has been successfully developed, thereby providing straightforward access to CF3‐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 CF3‐containing 1,3‐aminoalcohols. Powerful hybrid ligand: Cinchona‐alkaloid‐based sulfonamides were designed as effective hybrid ligands for copper, which enabled catalytic asymmetric radical oxytrifluoromethylation of alkenyl oximes to give CF3‐containing isoxazolines bearing α‐tertiary stereocenters with excellent yield and enantioselectivity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201804315