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

被引:72
作者
Wang, Yong-Bin [1 ]
Wu, Quan-Hao [1 ]
Zhou, Zhi-Peng [1 ]
Xiang, Shao-Hua [1 ,2 ]
Cui, Yuan [1 ]
Yu, Peiyuan [1 ]
Tan, Bin [1 ]
机构
[1] Southern Univ Sci & Technol, Shenzhen Grubbs Inst, Dept Chem, Shenzhen 518055, Peoples R China
[2] Southern Univ Sci & Technol, Acad Adv Interdisciplinary Studies, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
atropisomerism; chirality; cyclizations; heterocycles; organocatalysis; CATALYTIC ENANTIOSELECTIVE SYNTHESIS; ATROPOSELECTIVE SYNTHESIS; KINETIC RESOLUTION; LIGANDS; INDOLES; BIARYLS; ALKALOIDS; ARYLATION; PYRROLES; DESIGN;
D O I
10.1002/anie.201907470
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:13443 / 13447
页数:5
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