Palladium-Catalyzed (3+3) Annulation of Allenylethylene Carbonates with Nitrile Oxides
Ting Pan, Xing Gao, Sen Yang, Lan Wang, Yimin Hu, Min Liu, Wei Wang, Yongjun Wu, Bing Zheng, Hongchao Guo
Abstract
In this paper, we designed and synthesized a new type of cyclic carbonates, allenylethylene carbonates (AECs). With AECs as reactive precursors, we developed palladium-catalyzed (3+3) annulation of AECs with nitrile oxides. Various AECs worked well in this reaction under mild reaction conditions. A variety of 5,6-dihydro-1,4,2-dioxazine derivatives with allenyl quaternary stereocenters can be accessed in a facile manner in high yields (≤98%).
Topics & Concepts
AnnulationNitrileStereocenterChemistryPalladiumCatalysisCombinatorial chemistryOrganic chemistryEnantioselective synthesisCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms