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Updated: Jan 8, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Merging Aldehydic C-H Activation with Strain Release C-C Bond Cleavage of Bicyclo[1.1.0]butanes under Rh(III)
Tanmay Barman1, Om Prakash Dash1, Jatin Patra1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India.
Abstract:
Herein, we report a Rh(III)-catalyzed aldehydic C-H activation followed by strain release C-C cleavage of bicyclobutanes (BCBs) to access α-methylene-1,5-dicarbonyl motifs under mild conditions with excellent yields employing equimolar amounts of both reactants. This protocol is highly chemoselective and accommodates a wide variety of substrates. Synthetic utility of the developed protocol was demonstrated by carrying out gram scale synthesis and further functionalization of the final products. Additionally, α-methylene-1,5-dicarbonyl motifs obtained from amide BCBs undergo alkenyl C-H annulation with alkynes to afford substituted α-pyrones.
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