3 years ago

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

Base-Mediated Generation of Ketenimines from Ynamides: Direct Access to Azetidinimines by an Imino-Staudinger Synthesis
Pascal Retailleau, Mohamed Benchekroun, Corinne Minard, Robert H. Dodd, Kevin Cariou, Sandrine Ventre, Eugénie Romero
Ynamides were used as precursors for the in situ generation of highly reactive ketenimines that 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. Base Jump: Under strongly basic conditions ynamides gave highly reactive ketenimines that could be trapped with imines in a [2+2] cycloaddition. This imino-Staudinger synthesis led to a variety of imino analogues of β-lactams, namely azetidinimines (20 examples), that could be further functionalized through a broad range of transformations.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201702545

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