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Updated: Jul 5, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Low-valent titanium(II) mediated intramolecular and regioselective alkyne/alkoxyallene reductive coupling reactions
Florent Bodinier1, Marie-Isabelle Lannou1, Geoffroy Sorin1
1Unité CNRS UMR 8038 Université Paris Cité, Faculté de Pharmacie, Sorbonne Paris Cité, 4 avenue de l'Observatoire, PARIS 75270, cedex 06, France.
Abstract:
Low-valent titanium(II) complexes turned out to be suitable reagents in the promotion of alkyne/alkoxyallene coupling reactions in an intramolecular fashion. The conditions developed herein led to a broad range of highly functionalized cyclic adducts with excellent regioselectivities toward the central carbon of the alkoxyallene moiety. Good yields (up to 76%) were obtained over 19 examples. One-pot late functionalization by electrophile trapping was also possible and led to excellent diastereoselectivities (up to 95/5 d.r.).
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