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Updated: Sep 27, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Ir-Catalyzed cyclization of α,ω-dienes with an N-methyl group via two C-H activation steps
Katsumasa Tanaka1, Hiroshi Hattori1, Ryota Yabe1
1Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi, Osaka 558-8585, Japan. tnishi@sci.osaka-cu.ac.jp.
Abstract:
Iridium-catalyzed sp3 C-H alkylation of an N-methyl group with 1,5- and 1,6-dienes proceeded to give five- and six-membered carbocyclic compounds, respectively, in high yields. The reaction involves intermolecular alkylation of the N-methyl group with a vinyl moiety and subsequent intramolecular cyclization at the β-position of the initially formed alkylated intermediate. The reaction using a chiral bidentate phosphine ligand enabled the asymmetric synthesis of the cyclic compounds.
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