Carbene-Catalyzed Atroposelective Annulation and Desymmetrization of Urazoles
Jiamiao Jin, Xuan Huang, Jun Xu, Tingting Li, Xiaolin Peng, Xun Zhu, Junmin Zhang, Zhichao Jin, Yonggui Robin
Abstract
An NHC-catalyzed atroposelective reaction between ynals and urazoles is disclosed. The reaction establishes a chiral C-N axis via an atroposelective [3 + 2] annulation/desymmetrization process. Our reaction allows efficient access to axially chiral and heteroatom-rich urazole derivatives with potential applications in bioactive molecules and catalysis.
Topics & Concepts
DesymmetrizationAnnulationChemistryCarbeneCatalysisHeteroatomCombinatorial chemistryOrganocatalysisMoleculeOrganic chemistryEnantioselective synthesisRing (chemistry)N-Heterocyclic Carbenes in Organic and Inorganic ChemistryAxial and Atropisomeric Chirality SynthesisSynthetic Organic Chemistry Methods