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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Copper-Catalyzed Enantioselective ε-Site Yne-Allylic Amination
Chaochao Yao1, Kongling Feng1, Yuepeng Lu1
1Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, State Key Laboratory of Green Pesticide, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan 430079, P. R. China.
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The development of highly selective and sustainable catalytic methods for the synthesis of enantiomerically chiral amines is of great interest and importance in both the pharmaceutical and fine chemical industries. Here, we have developed a remote asymmetric copper-catalyzed ε-site yne-allylic amination of yne-allylic esters. With earth-abundant metal copper catalysts, a wide range of yne-allylic esters and aliphatic amines can be efficiently converted into highly enantioenriched chiral amines products. Moreover, the vitally important transformation of enantioenriched tertiary amines into optically active primary amines further demonstrates the synthetic utility of this method in the preparation of various synthetic building blocks, ligands, and drugs.
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