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Updated: Jun 23, 2025
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
General Regio- and Diastereoselective Allylic C-H Oxygenation of Internal Alkenes
Kyohei Yamada1, Kelvin Pak Shing Cheung1, Vladimir Gevorgyan1
1Department of Chemistry and Biochemistry, The University of Texas at Dallas, 800 West Campbell Road, Richardson, Texas 75080-3021, United States.
Abstract:
Branched allylic esters and carboxylates are fundamental motifs prevalent in natural products and drug molecules. The direct allylic C-H oxygenation of internal alkenes represents one of the most straightforward approaches, bypassing the requirement for an allylic leaving group as in the classical Tsuji-Trost reaction. However, current methods suffer from limited scope─often accompanied by selectivity issues─thus hampering further development. Herein we report a photocatalytic platform as a general solution to these problems, enabling the coupling of diverse internal alkenes with carboxylic acids, alcohols, and other O-nucleophiles, typically in a highly regio- and diastereoselective manner.
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