Regioselective Formal [3+2] Cycloadditions of Urea Substrates with Activated and Unactivated Olefins for Intermolecular Olefin Aminooxygenation

Angew Chem Int Ed Engl. 2019 Aug 19;58(34):11676-11680. doi: 10.1002/anie.201904662. Epub 2019 Jul 17.


A new class of intermolecular olefin aminooxygenation reaction is described. This reaction utilizes the classic halonium intermediate as a regio- and stereochemical template to accomplish the selective oxyamination of both activated and unactivated alkenes. Notably, urea chemical feedstock can be directly introduced as the N and O source and a simple iodide salt can be utilized as the catalyst. This formal [3+2] cycloaddition process provides a highly modular entry to a range of useful heterocyclic products with excellent selectivity and functional-group tolerance.

Keywords: alkenes; aminooxygenation; cycloaddition; homogeneous catalysis; oxazoline.