Metal-Free Aerobic Radical Ring Opening–Cyclization of Bicyclo[1.1.0]butylamides to Oxazolidin-4-ones
Abstract
Bicyclo[1.1.0]butane (BCB) is a highly strained compound with unique reactivity. In this work, we discovered that a BCB derivative bearing an aryl and a diisopropylamide group undergoes an oxygen-mediated transformation to give the corresponding oxazolidin-4-one derivative in good yield under mild conditions (EtOAc, O2, 40 °C). The structure of the product was confirmed by X-ray crystallographic analysis, and radical trapping experiments suggested that the reaction involves a radical pathway. This reaction enables direct conversion of BCB carbon atoms into a heterocyclic scaffold with a high atom economy.
Fields of Study & Subjects
Oxidative Organic Chemistry Reactions
Cyclopropane Reaction Mechanisms
Radical Photochemical Reactions
Publication details
- Journal / source
- Chemical and Pharmaceutical Bulletin
- Volume
- 74
- Issue
- 2
- Pages
- 153–156
- Publication date
- 5 February 2026
- Language
- EN