Asymmetric Construction of Axially Chiral 2‐Arylpyrroles by Chirality Transfer of Atropisomeric Alkenes. (12th August 2019)

• Record Type: Journal Article
• Authors: Wang, Yong‐Bin; Wu, Quan‐Hao; Zhou, Zhi‐Peng; Xiang, Shao‐Hua; Cui, Yuan; Yu, Peiyuan; Tan, Bin
• Is Part Of: Angewandte Chemie. Volume 131:Number 38(2019)
• Page Start: 13577
• Page End: 13581
• Publication Date: 2019-08-12
• Subjects: Atropisomerie -- Chiralität -- Cyclisierungen -- Heterocyclen -- Organokatalyse; Chemistry -- Periodicals; 540
• DOI: 10.1002/ange.201907470
• Languages: English
• ISSNs: 0044-8249

Abstract

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. Abstract : Axial‐chirale 2‐Arylpyrrole sind über einen direkten Chiralitätstransfer durch schnelle Cyclisierung von enantiomerenangereicherten atropisomeren Alkenen zugänglich, die durch organokatalytische asymmetrische N‐Alkylierung erzeugt werden. Aus den Produkt‐Alkenen konnten neue heterocyclische 2‐Arylazepin‐Atropisomere durch eine rational entwickelte En‐Reaktion hergestellt werden.