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Updated: Jun 16, 2026
Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Diastereodivergent Hydroamidation of Methylenecyclohexanes With Differentiated Active Catalytic Species
Zhen Li1, Yi-Zhou Tong1, Kai-Ran Duan1
1State Key Laboratory of Precision and Intelligent Chemistry, Anhui Province Key Laboratory of Biomass Chemistry, University of Science and Technology of China, Hefei, China.
Abstract:
The construction of three-dimensional (3D) organic molecular structures is pivotal in modern organic chemistry. For three dimensionally structured disubstituted cyclohexanes, which exist as two possible configurations (cis- and trans-), substituent orientation dictates thermodynamic stability, physicochemical properties, and biological activities, but precise stereocontrol of cycloalkane substituents is challenging. Herein, we report the diastereodivergent hydroamidation of methylenecyclohexanes: a nickel catalytic system efficiently synthesizes 1,4-cis/trans and 1,3-cis/trans isomers, while a cobalt system realizes 1,2-cis/trans stereodivergence. The core achievement lies in a strategy utilizing differentiated active catalytic species, which enables the precise regulation of the spatial structure and electronic properties of metal-hydride or metal-functional group intermediates. This work broadens the chemical space for multi-substituted cyclohexane synthesis, provides a powerful tool for the preparation of cycloalkyl-containing drug molecules, and offers an important case for research on substituted cyclohexane stereochemistry.
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