Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (6): 1522-1528.DOI: 10.6023/cjoc201904030 Previous Articles     Next Articles

Special Issue: 金属有机化学

Reviews

含有五元杂芳结构的联芳轴手性化合物的对映选择性合成

张硕, 廖港, 史炳锋   

  1. 浙江大学化学系 杭州 310027
  • 收稿日期:2019-04-11 修回日期:2019-05-06 出版日期:2019-06-25 发布日期:2019-05-10
  • 通讯作者: 史炳锋 E-mail:bfshi@zju.edu.cn
  • 基金资助:

    国家重点基础研究发展计划(No.2015CB856600)、国家自然科学基金(Nos.21772170,21572201)、中央高校基本科研业务费(No.2018XZZX001-02)、浙江省自然科学基金(No.LR17B020001)和中国博士后科学基金(No.2019M650135)资助项目.

Enantioselective Synthesis of Atropisomers Featuring Pentatomic Heteroaromatics

Zhang Shuo, Liao Gang, Shi Bingfeng   

  1. Department of Chemistry, Zhejiang University, Hangzhou 310027
  • Received:2019-04-11 Revised:2019-05-06 Online:2019-06-25 Published:2019-05-10
  • Contact: 10.6023/cjoc201904030 E-mail:bfshi@zju.edu.cn
  • Supported by:

    Project supported by the National Basic Research Program of China (No. 2015CB856600), the National Natural Science Foundation of China (Nos. 21772170, 21572201), the Fundamental Research Funds for the Central Universities (No. 2018XZZX001-02), the Natural Science Foundation of Zhejiang Province (No. LR17B020001) and the China Postdoctoral Science Foundation (No. 2019M650135).

Axially chiral biaryl skeletons are ubiquitous stuctural motifs that are widely represented in pharmaceuticals and natural products, and have been widely used as privileged chiral ligands/catalysts in asymmetric synthesis. Therefore, the asymmetric construction of these compounds has received tremendous attention. However, the established strategies are mainly limited to the construction of biaryls containing hexatomic aromatics, and the approaches towards atropisomers featuring pentatomic heteroaromatics connected through C-C or C-N bond have emerged gradually only until recently. The main hurdle is basically due to the increased distance of substituents ortho to the axis, which is responsible for lower barriers to rotation, thus rendering the asymmetric synthesis more challenging. This review summarizes recent advances on the enantioselective synthesis of atropisomers featuring pentatomic heteroaromatics.

Key words: atropisomers featuring pentatomic heteroaromatic, enantioselective synthesis, axial chirality, biaryl