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Updated: Jul 20, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Enantioselective Dearomatization of Substituted Phenols via Organocatalyzed Electrophilic Amination
Zidan Ye1, Wei Liu1, Huanchao Gu1
1School of Physical Science and Technology, ShanghaiTech University, Shanghai 201210, China.
Abstract:
Highly efficient and stereoselective dearomatization of substituted phenols was achieved via chiral phosphoric acid-catalyzed electrophilic para-amination with commercially available azodicarboxylates. This protocol readily afforded a series of chiral 2,5-cyclohexadienones bearing 4-aza-quaternary stereocenters with excellent yields and enantioselectivities (≤99% yield and >99% ee). Easy scale-up of this reaction to a gram scale and diverse derivatizations of the chiral products into α-tertiary amines and α-tertiary heterocycles derivatives well demonstrated the potential of this method.
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