Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones

Reaction of Ynamides with Iminoiodinane-Derived Nitrenes: Formation of Oxazolones and Polyfunctionalized Oxazolidinones
Pascal Retailleau, Loïc Habert, Isabelle Gillaizeau, Philippe Dauban, Benjamin Darses, Gwendal Grelier, Romain Rey-Rodriguez
This article describes the reaction of ynamides with metallanitrenes generated in the presence of an iodine(III) oxidant. N-(Boc)-Ynamides are converted to oxazolones via a cyclization reaction. The reaction is mediated by a catalytic dirhodium-bound nitrene species that first behaves as a Lewis acid. The oxazolones can be converted in a one pot manner to functionalized oxazolidinones following a regio- and stereoselective oxyamination reaction with the same nitrene reagent generated in stoichiometric amounts.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01623

DOI: 10.1021/acs.joc.7b01623

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