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Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes
Article de revue   Open Access   Avec comité de lecture

Transition-Metal-Free α-Vinylation of Enolizable Ketones with β-Bromostyrenes

Yassir Zaid, Clève Dionel Mboyi, Martin Pichette Drapeau, Léa Radal, Fouad Ouazzani Chahdi, Youssef Kandri Rodi, Thierry Ollevier et Marc Taillefer
Organic Letters, Vol.21(6), pp.1564-1568
04/03/2019

Résumé

An α-vinylation of enolizable ketones has been developed by using β-bromostyrenes and a KOtBu/NMP system. β,γ-Unsaturated ketones of E configuration were obtained in excellent yield and selectivity. Further synthetic possibilities are highlighted by one-pot functionalization via trapping of intermediate dienolates with alkyl, allyl, benzyl, and propargyl halides to generate quaternary centers. The reported transformation is believed to involve phenylacetylene and propargylic alcohol derivatives.

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