Radical Chain Isomerization of <i>N</i>-Sulfonyl Ynamides to Ketenimines and Its Application to Furan Dearomatization
Jiahuan Shen, Zhenhua Wu, Yi Liu, Yihui Bai, Jiayan Qiu, Zuxiao Zhang, Zheliang Yuan, Gangguo Zhu
Abstract
-sulfonyl ynamides to isolable ketenimines is developed, featuring mild reaction conditions, a high efficiency, ∼100% atom economy, a broad substrate scope, and column chromatography-free workup in most cases. Meanwhile, an unprecedented dearomatization of furans is achieved by the radical chain isomerization-triggered aza-Claisen rearrangement, providing highly chemo-, regio-, stereo-, and diastereoselective access to functionalized quaternary nitriles.
Topics & Concepts
IsomerizationChemistryFuranSulfonylMedicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisAlkylCatalytic Alkyne ReactionsSulfur-Based Synthesis TechniquesCyclopropane Reaction Mechanisms