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Updated: Sep 8, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium-Catalyzed Z-Alkenyl 1,3-Migration
Xue-Mei Huang1, Si-Qi Xiong1, Zi-Xin Ye1
1School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, P. R. China.
Abstract:
Strategies for the selective cleavage of inert C-C bonds in tertiary alcohols have been developed. However, a gap remains in Z-alkenyl 1,3-migration through selective C(sp3)-C(Z-alkenyl) bond cleavage. Herein, we report rhodium-catalyzed Z-alkenyl 1,3-migration, which efficiently yields (Z)-γ,δ-unsaturated ketones. The success of the transformation could be attributed to selective C(sp3)-C(Z-alkenyl) bond cleavage. In this study, we disclose that the migration order in this catalytic system is Z-alkenyl, E-alkenyl, and aryl (alkyl), in decreasing reactivity. This catalytic system has the advantages of good functional group compatibility, a wide range of substrates, and mild reaction conditions.
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