Atroposelective Access to Dihydropyridinones with C–N Axial and Point Chirality via NHC-Catalyzed [3 + 3] Annulation
Yanting Li, Xiaoyong Duan, Chengxian Yang, Yamei Wei, Jiahan Li, Xiaojie Ren, Jing Qi
Abstract
-heterocyclic carbene-catalyzed atroposelective [3 + 3] annulation of enals with 2-aminomaleate derivatives is described. A series of substituted dihydropyridones bearing both C-N axis and point chirality were synthesized with good diastereo- and enantioselectivity under mild conditions. This efficient strategy successfully superpositions an extra point chiral element with an axial backbone, and the generated structurally interesting atropisomers may have potential application in drug discovery.
Topics & Concepts
AnnulationAtropisomerAxial chiralityChemistryCarbeneChirality (physics)CatalysisStereochemistryCombinatorial chemistryEnantioselective synthesisOrganic chemistryParticle physicsPhysicsQuarkChiral symmetry breakingNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisSynthetic Organic Chemistry MethodsAsymmetric Synthesis and Catalysis