<i>N</i>-Heterocyclic Carbene-Catalyzed Atroposelective Synthesis of Axially Chiral α-Carbolinones via Heterocycle Formation
Haiying Wang, Zhicheng Li, Chun-Lin Zhang, Song Ye
Abstract
An NHC-catalyzed atroposelective synthesis of axially chiral α-carbolinones from α,β-unsaturated iminoindole derivatives and α-chloroaldehydes was developed. The reaction proceeds through a cascade process including [4 + 2] annulation and then oxidative dehydrogenation with concomitant central-to-axial chirality conversion under mild conditions. The developed method opens a new avenue to efficiently access axially chiral α-carbolinones in moderate to good enantioselectivities.
Topics & Concepts
Axial symmetryAxial chiralityAnnulationCarbeneChemistryCatalysisDehydrogenationCascadeCombinatorial chemistryChirality (physics)Organic chemistryEnantioselective synthesisPhysicsParticle physicsChiral perturbation theoryQuantum mechanicsPionChromatographyNambu–Jona-Lasinio modelAxial and Atropisomeric Chirality SynthesisAlgebraic structures and combinatorial modelsAsymmetric Synthesis and Catalysis