Angewandte Chemie International Edition · 2019 · 105 citations · 60 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryDiversity-oriented SynthesisHeterocycle SynthesisAsymmetric Heterocycle SynthesisAsymmetric StrategyAsymmetric SynthesisChiralityPyrrole ChemistryPyrrole Synthesis
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 · 520 citations
Organocatalytic asymmetric arylation of indoles enabled by azo groups
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