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Updated: Jul 11, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinones with vinylene carbonate
1Key Laboratory of Chemical Additives for China National Light Industry, College of Chemistry and Chemical Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China. nanjiang@sust.edu.cn.
Abstract:
Herein, a novel organic transformation involving rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinone with vinylene carbonate is reported, and a series of architecturally rigid and widely used spirolactams are obtained with excellent functional group tolerance and high selectivity. Remarkably, the promising vinylene carbonate reagent presents a distinct chemical reactivity as a vinyl-oxygen cyclic synthon and first transfers the C-H bond to spiroheterocycle scaffolds. Moreover, another chemoselectivity, direct dehydrogenative coupling with vinylene carbonate, is also presented. This protocol is compatible with green chemistry and only releases H2O and CO2 as byproducts.
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