Abstract
1,3-Dienes are vital building blocks in organic synthesis. They underpin many fundamental synthetic transformations and are present in numerous natural products and drug candidate molecules. The rearrangement of an alkylallene to a 1,3-diene is an atom efficient, redox neutral, transformation that provides a straightforward synthetic route to functionalized 1,3-dienes. Herein, we provide an account of this transformation using allenes that are not predisposed by the presence of heteroatoms or electron-withdrawing groups directly attached to the allene. Early reports of this skeletal rearrangement are acid-mediated approaches, with limited substrate scope, but they provide valuable mechanistic insights. More recent transition metal-mediated approaches that exhibit improved substrate scope are described, together with isolated examples that have utilized this rearrangement.
Highlights
IntroductionThe and a recent extensive review, centered on stereoselective providesmotif an excellent application of olefination strategies has dominated their synthesis [11,12,13,14,15,16]; this was subaccount of current synthetic approaches to the 1,3-diene motif [10]
Ment through direct attachment of heteroatoms or electron-withdrawing groups (e.g., 3e). The rearrangement of this allene class has been a focus of interest since the early 1960s, The rearrangement of this allene class has been a focus of interest since the early and it is only recently that its synthetic potential has been improved
An Au(III)-catalyzed of activation aryl-substituted. Due to their carbophilic attack character, catalysts are idealrearrangement for the selective. Due to their carbophilic character, gold catalysts are ideal for the selective activation allenes to 1,3-dienesattack was accomplished by Liu et al.rearrangement (Scheme 12) [60,61]
Summary
The and a recent extensive review, centered on stereoselective providesmotif an excellent application of olefination strategies has dominated their synthesis [11,12,13,14,15,16]; this was subaccount of current synthetic approaches to the 1,3-diene motif [10]. Ment through direct attachment of heteroatoms or electron-withdrawing groups (e.g., 3e) The rearrangement of this allene class has been a focus of interest since the early 1960s, The rearrangement of this allene class has been a focus of interest since the early and it is only recently that its synthetic potential has been improved.
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