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
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 chiralityCarbeneChemistryCatalysisChirality (physics)CycloadditionDerivative (finance)Combinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryEnantioselective synthesisPhysicsNambu–Jona-Lasinio modelEconomicsChiral symmetry breakingQuantum mechanicsQuarkFinancial economicsAxial and Atropisomeric Chirality SynthesisCatalytic C–H Functionalization MethodsSynthesis of heterocyclic compounds