Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino Staudinger Synthesis - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2017

Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino Staudinger Synthesis

Eugénie Romero
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  • IdRef : 193045931
Mohamed Benchekroun
Sandrine Ventre
  • Fonction : Auteur
Robert H Dodd
  • Fonction : Auteur
Kevin Cariou

Résumé

Ynamides were used as precursors for the in situ generation of highly reactive ketenimines which could be trapped with imines in a [2+2] cycloaddition. This imino Staudinger synthesis led to a variety of imino-analogs of β-lactams, namely azetidinimines (20 examples), that could be further functionalized through a broad range of transformations. Ynamides (1) are versatile nitrogen-containing building blocks composed of an acetylene moiety directly attached to a nitrogen atom that generally bears at least one electron-withdrawing group that stabilizes the molecules.

Domaines

Chimie organique
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Dates et versions

hal-02307210 , version 1 (07-10-2019)

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Citer

Eugénie Romero, Corinne Minard, Mohamed Benchekroun, Sandrine Ventre, Pascal ́ Retailleau, et al.. Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino Staudinger Synthesis. Chemistry - A European Journal, 2017, 23 (53), pp.12991-12994. ⟨10.1002/chem.201702545⟩. ⟨hal-02307210⟩
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