Synthesis of Enantiopure Hydrocarbon Cages Based on an Optically Resolved C3-Symmetric Triaminotribenzotriquinacene

Zhi-Qiang Zhang; Qing-Xia Ren; Wan-Fa Tian; Wen-Hua Sun; Xiao-Ping Cao; Zi-Fa Shi; Hak-Fun Chow; Dietmar Kuck

doi:10.1021/acs.orglett.1c00176

Synthesis of Enantiopure Hydrocarbon Cages Based on an Optically Resolved C₃-Symmetric Triaminotribenzotriquinacene

Org Lett. 2021 Feb 19;23(4):1478-1483. doi: 10.1021/acs.orglett.1c00176. Epub 2021 Feb 2.

Authors

Zhi-Qiang Zhang¹, Qing-Xia Ren¹, Wan-Fa Tian¹, Wen-Hua Sun², Xiao-Ping Cao¹, Zi-Fa Shi¹, Hak-Fun Chow³, Dietmar Kuck⁴

Affiliations

¹ State Key Laboratory of Applied Organic Chemistry and College of Chemistry & Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. China.
² Beijing National Laboratory for Molecular Sciences, Key Laboratory for Engineering Plastics, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, P. R. China.
³ Department of Chemistry and State Key Laboratory of Synthetic Chemistry, The Chinese University of Hong Kong, Shatin, NT, Hong Kong.
⁴ Department of Chemistry and Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany.

PMID: 33525871
DOI: 10.1021/acs.orglett.1c00176

Abstract

The synthesis of the enantiomerically pure, D₃-symmetric covalent hydrocarbon cages (+)-(M,M)-4 and (-)-(P,P)-4 bearing two C₃-symmetrically functionalized tribenzobenzotriquinacene (TBTQ) vertices is reported. The enantiomerically pure TBTQ building blocks (+)-(M)-5 and (-)-(P)-5 were prepared via the diastereomeric TBTQ triamides obtained by use of both Boc-d- and Boc-l-phenylglycine as chiral auxiliaries.