Issue 28, 2021

Phosphine-catalysed (4+1) annulations of β′-acetoxy allenoate with β,γ-unsaturated carbonyl compounds

Abstract

While β,γ-unsaturated carbonyl compounds have been widely used as γC- or αC-nucleophiles, their potential αC,αC-bisnucleophilic reactivity is still underdeveloped. Herein, a phosphine-catalysed (4+1) annulation of β′-acetoxy allenoate and a β,γ-unsaturated carbonyl compound is reported, wherein β′-acetoxy allenoate is the 1,4-biselectrophilic component while the β,γ-unsaturated carbonyl compound serves as an αC,αC-bisnucleophile. The process not only provides a new reaction mode of β,γ-unsaturated carbonyl compounds under mild conditions but also broadens the scope of Lewis base-catalysed annulation of acetoxy allenoate.

Graphical abstract: Phosphine-catalysed (4+1) annulations of β′-acetoxy allenoate with β,γ-unsaturated carbonyl compounds

Supplementary files

Article information

Article type
Communication
Submitted
21 Jan 2021
Accepted
08 Feb 2021
First published
05 Mar 2021

Chem. Commun., 2021,57, 3488-3491

Phosphine-catalysed (4+1) annulations of β′-acetoxy allenoate with β,γ-unsaturated carbonyl compounds

Y. Zhang, D. Wang and X. Tong, Chem. Commun., 2021, 57, 3488 DOI: 10.1039/D1CC00368B

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