Relay Annulation of Ammonium Ylides with Oxindole-Derived α,β-Unsaturated Ketimines: Catalytic Construction of Spiro-polycyclic Oxindoles
Weihao Zheng, Jingfang Lv, Shi-Mei He, Ning Yu, Yuqiang Zhou, Yunbo Yang, Lv-Yan Liu, Kui-Cheng He, Ye Wei, Kun Jiang
Abstract
An ammonium ylide-based relay annulation was disclosed, which uses DABCO as the catalyst and oxindole-derived α,β-unsaturated ketimines and γ-bromo-crotonates as the starting materials. This method enables the rapid assembly of a series of structurally novel spiro-polycyclic oxindoles containing a bicyclo[4.1.0]heptane moiety through simultaneous generation of three new bonds and two rings in one step under mild reaction conditions.
Topics & Concepts
OxindoleAnnulationChemistryDABCOCatalysisMoietyYlideHeptaneOrganocatalysisAmmoniumCombinatorial chemistryOrganic chemistryEnantioselective synthesisCyclopropane Reaction MechanismsAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions