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Updated: Jun 30, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Regio- and Chemoselective Double Allylic Substitution of Alkenyl vic-Diols
Bocheng Chen1, Lucas Pagès1, Raphaël Dollet1
1Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO, UMR 8182), Université Paris-Saclay, CNRS, 15, rue Georges Clémenceau, 91405 Cedex Orsay, France.
Abstract:
Double allylic substitution is an attractive approach to building molecular complexity from simple starting materials by creating two new bonds in one pot. However, this type of reaction has been doomed by chemoselectivity and regioselectivity issues. In this letter, we describe a new approach to introduce a-la-carte two new C-C, C-N, C-O, or C-S bonds in a chemo- and regioselective fashion. The reaction relies on sequential dual catalysis with a Lewis acid and palladium. The scope is remarkably broad, and the reaction can be diastereoselective by using secondary alcohols as the first nucleophile.
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