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

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.

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

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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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