Regio-and Chemoselective Double Allylic Substitution of Alkenyl vic-Diols - Archive ouverte HAL
Article Dans Une Revue Organic Letters Année : 2024

Regio-and Chemoselective Double Allylic Substitution of Alkenyl vic-Diols

Résumé

Double allylic substitution is an attractive approach to build 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 manuscript, 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 Lewis acid and palladium. The scope is remarkably broad, and the reaction can be diastereoselective using secondary alcohols as the first nucleophile.

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Chimie
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Dates et versions

hal-04727504 , version 1 (09-10-2024)

Identifiants

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Bocheng Chen, Lucas Pagès, Raphaël Dollet, Cyrille Kouklovsky, Sébastien Prévost, et al.. Regio-and Chemoselective Double Allylic Substitution of Alkenyl vic-Diols. Organic Letters, 2024, 26 (12), pp.2393-2397. ⟨10.1021/acs.orglett.4c00495⟩. ⟨hal-04727504⟩
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