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 which were trapped with imines in a [2+2] cycloaddition under microwave irradiation. Twenty novel azetidinimines have been prepared in this straightforward and operationally simple manner. Furthermore, the products arising from this imino-Staudinger synthesis were functionalized using a wide range of protocols that leave the four-membered amidine ring intact. (Illustration by E. Menneteau, CNRS-PRC 2017). More information can be found in the Communication by R. H. Dodd, K. Cariou et al. (DOI: 10.1002/chem.201702545).

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

DOI: 10.1002/chem.201703248

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