Wang Yong-Bin, Wu Quan-Hao, Zhou Zhi-Peng, Xiang Shao-Hua, Cui Yuan, Yu Peiyuan, Tan Bin
Shenzhen Grubbs Institute, Department of Chemistry, Southern University of Science and Technology, Shenzhen, 518055, P. R. China.
Academy for Advanced Interdisciplinary Studies, Southern University of Science and Technology, Shenzhen, 518055, P. R. China.
Angew Chem Int Ed Engl. 2019 Sep 16;58(38):13443-13447. doi: 10.1002/anie.201907470. Epub 2019 Aug 12.
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.
通过对映体富集的阻转异构烯烃的快速环化反应,采用直接手性转移策略可高效构建轴向手性2-芳基吡咯骨架,这些对映体富集的阻转异构烯烃是通过有机催化的不对称N-烷基化反应生成的。该方法适用于广泛的底物,具有极高的手性转移效率,可提供具有完全取代吡咯部分和高对映体纯度的新型阻转异构体。鉴于对映体富集的阻转异构烯烃,通过合理设计的烯反应实现了新型杂环2-芳基氮杂卓阻转异构体。