Iminoxyl Radical-Promoted Oxycyanation and Aminocyanation of Unactivated Alkenes: Synthesis of Cyano-Featured Isoxazolines and Cyclic Nitrones

• DOI: 10.1021/acs.orglett.7b00826
• Publication Date: 2017-06-07T17:45:08Z
• Authors: Fei Chen; Fei-Fei Zhu; Man Zhang; Rui-Hua Liu; Wei Yu; Bing Han
• Keywords: 01 natural sciences; 3. Good health; 0104 chemical sciences

A novel and facile approach to vicinal oxycyanation and aminocyanation of internal unactivated alkenes is developed. This method utilizes the dichotomous reactivity of iminoxyl radical derived from the initiation of β,γ- and γ,δ-unsaturated ketoximes to provide the general difunctionalization of internal alkenes using tert-butyl hydroperoxide (TBHP) as the environmentally friendly oxidant, CuCN as the commercially available cyanating reagent, and pentamethyldiethylenetriamine (PMDETA) as the ligand. By using this protocol, a series of useful cyano-featured isoxazolines and cyclic nitrones were efficiently prepared.