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Asymmetric Construction of Axially Chiral 2-Arylpyrroles by Chirality Transfer of Atropisomeric Alkenes.

Yong-Bin WangQuan-Hao WuZhi-Peng ZhouShao-Hua XiangYuan CuiPeiyuan YuBin Tan
Published in: Angewandte Chemie (International ed. in English) (2019)
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.
Keyphrases
  • electron transfer
  • ionic liquid
  • capillary electrophoresis
  • solid state
  • loop mediated isothermal amplification
  • molecular dynamics simulations