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Asymmetric Construction of Axially Chiral 2‐Arylpyrroles by Chirality Transfer of Atropisomeric Alkenes
Author(s) -
Wang YongBin,
Wu QuanHao,
Zhou ZhiPeng,
Xiang ShaoHua,
Cui Yuan,
Yu Peiyuan,
Tan Bin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201907470
Subject(s) - atropisomer , chirality (physics) , axial chirality , chemistry , moiety , enantioselective synthesis , combinatorial chemistry , stereochemistry , catalysis , organic chemistry , physics , chiral symmetry breaking , quantum mechanics , nambu–jona lasinio model , quark
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.