N‐Heterocyclic Carbene‐Catalyzed Atroposelective Annulation for Access to Thiazine Derivatives with C−N Axial Chirality
Tingting Li, Chengli Mou, Pu‐Ying Qi, Xiaolin Peng, Shichun Jiang, Ge‐Fei Hao, Wei Xue, Song Yang, Hao Lin, Yonggui Robin, Zhichao Jin
Abstract
A catalytic atroposelective cycloaddition reaction between thioureas and ynals is developed. This reaction features the first NHC-catalyzed addition of thioureas to acetylenic acylazolium intermediates to eventually set up C-N axial chirality with excellent optical purities. The obtained axially chiral thiazine derivative products bear multiple functional groups and are feasible for further transformations.
Topics & Concepts
AnnulationThiazineAxial chiralityCarbeneCatalysisChemistryChirality (physics)CycloadditionDerivative (finance)Combinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryEnantioselective synthesisPhysicsNambu–Jona-Lasinio modelChiral symmetry breakingQuarkFinancial economicsQuantum mechanicsEconomicsAxial and Atropisomeric Chirality SynthesisN-Heterocyclic Carbenes in Organic and Inorganic ChemistrySynthesis of heterocyclic compounds