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

Yong‐Bin Wang, Quan‐Hao Wu, Zhipeng Zhou, Shao‐Hua Xiang, Yuan Cui, Peiyuan Yu, Bin Tan

Angewandte Chemie International Edition · 2019 · 105 citations · 60 references

Concepts

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.

References

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