An orthogonal reactivity of diazo compounds toward azirine-2-carboxylic acids, switching with the reaction conditions, is demonstrated. A gold-catalyzed reaction is N selective and produces 1,3-oxazin-6-ones, whereas a blue light activation leads to O−H insertion products, azirine-2-carboxylic esters. The observed chemodivergence is explained by the metalbound and metal-free carbenes exhibiting different electronic properties in these reactions. In addition, a high antibacterial potential of the 1,3-oxazin-6-ones synthesized is shown.
Original languageEnglish
Pages (from-to)2707−2712
JournalOrganic Letters
Volume25
Issue number15
StatePublished - 6 Apr 2023

ID: 105363083