Angewandte Chemie · 2019 · 31 citations · 59 references
Asymmetric CatalysisDerivativesEngineeringNatural SciencesDiversity-oriented SynthesisRapid CyclizationOrganic ChemistryNovel AtropisomersEnantioenriched Atropisomeric AlkenesAtropisomeric AlkenesChemistryHeterocycle ChemistrySynthetic ChemistryChirality TransferStereoselective SynthesisAsymmetric ConstructionEnantioselective SynthesisBiomolecular Engineering
Abstract Axially chiral 2‐arylpyrrole frameworks are efficiently accessed through a direct chirality transfer strategy by rapid cyclization of enantioenriched atropisomeric alkenes, which are generated by organocatalytic asymmetric N‐alkylation reactions. This approach accommodates a broad scope of substrates with remarkably high chirality transfer efficiency, affording novel atropisomers with a fully substituted pyrrole moiety and high enantiopurities. Given the enantioenriched atropisomeric alkenes, novel heterocyclic 2‐arylazepine atropisomers were realized through a rationally designed ene reaction.
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Revealing Atropisomer Axial Chirality in Drug Discovery
Steven R. LaPlante, Paul Edwards, Lee D. Fader et al. · ChemMedChem · 2011 · 499 citations
Molecular Pharmacology, Medicinal Chemistry, Molecular Sciences +15
Organocatalytic asymmetric arylation of indoles enabled by azo groups
Liangwen Qi, Jianhui Mao, Jian Zhang et al. · Nature Chemistry · 2017 · 357 citations