From Alkenes to Isoxazolines via Copper-Mediated Alkene Cleavage and Dipolar Cycloaddition

• DOI: 10.1021/acs.orglett.9b02748
• Publication Date: 2019-09-11T19:12:35Z
• Authors: Mingchun Gao; Yuansheng Gan; Bin Xu
• Keywords: Alkene; Cleavage (geology); Bond cleavage

An unprecedented copper-mediated anion transformation is reported, along with selective C═C double bond cleavage and dipolar cycloaddition reaction from simple alkenes inexpensive copper nitrate. Various transformations demonstrate the generality of this method. Further mechanistic investigation indicates a novel ionic pathway for alkene highlights coeffect iodide boric acid as additives on inhibition well-documented competitive nitration byproducts.