Synthesis and Resolution of Optically Active Topologically Chiral Catenane

被引:3
|
作者
Ishizu, Yuki [1 ]
Takeyoshi, Ayaka [1 ]
Hasegawa, Eietsu [1 ]
Iwamoto, Hajime [1 ]
机构
[1] Niigata Univ, Grad Sch Sci & Technol, Dept Chem, Nishi Ku, 8050 Ikarashi 2 No Cho, Niigata 9502181, Japan
基金
日本学术振兴会;
关键词
Catenane; Topological chirality; Chiral auxiliary; METATHESIS CATALYSTS; MOLECULAR MACHINES;
D O I
10.1246/cl.200555
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A topologically chiral [2]catenane was synthesized and resolved by a diastereomer method. The [2]catenane consisting of a C-s symmetrical crown ether and a C-s symmetrical ammonium macrocycle was obtained as a racemic mixture. Introduction of a chiral auxiliary to the [2]catenane gave a diastereomeric mixture which was successfully resolved. Removal of the chiral auxiliary from both enantiomers of the [2]catenane gave rise to minor images of their CD spectra.
引用
收藏
页码:1435 / 1438
页数:4
相关论文
共 50 条
  • [1] A Co-conformationally "Topologically" Chiral Catenane
    Rodriguez-Rubio, Arnau
    Savoini, Andrea
    Modicom, Florian
    Butler, Patrick
    Goldup, Stephen M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (27) : 11927 - 11932
  • [2] Synthesis of optically active δ-elodecalactone via chiral resolution using CPF
    Nemoto, Hisao
    Zhong, Weihui
    Kawamura, Tomoyuki
    Kamiya, Masaki
    Nakano, Yasushi
    Sakamoto, Kei
    SYNLETT, 2007, (15) : 2343 - 2346
  • [3] Inducing and Switching the Handedness of Polyacetylenes with Topologically Chiral [2]Catenane Pendants
    Wang, Yu
    Zhang, Xin
    Huang, Chang-Bo
    Hu, Lianrui
    Wang, Xu-Qing
    Wang, Wei
    Yang, Hai-Bo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (37)
  • [4] RESOLUTION AND SYNTHESIS OF AN OPTICALLY ACTIVE FLUOROCOMPLEX
    BASALO, F
    MATOUSH, WR
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1955, 67 (14-5) : 402 - 402
  • [5] Regioselective template synthesis, X-ray structure, and chiroptical properties of a topologically chiral sulfonamide catenane
    Mohry, A
    Vögtle, F
    Nieger, M
    Hupfer, H
    CHIRALITY, 2000, 12 (02) : 76 - 83
  • [6] Synthesis of optically active chiral shell dendrons
    Junge, DM
    McGrath, DV
    TETRAHEDRON LETTERS, 1998, 39 (13) : 1701 - 1704
  • [8] Enantiomeric resolution of cycloenantiomeric rotaxane, topologically chiral catenane, and pretzel-shaped molecules: Observation of pronounced circular dichroism
    Yamamoto, C
    Okamoto, Y
    Schmidt, T
    Jager, R
    Vogtle, F
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (43) : 10547 - 10548
  • [9] Triphasic circularly polarized luminescence switch quantum simulation of a topologically chiral catenane
    Bella, Giovanni
    Milone, Marco
    Bruno, Giuseppe
    Santoro, Antonio
    JOURNAL OF MATERIALS CHEMISTRY C, 2024, 12 (08) : 3005 - 3012
  • [10] AN OPTICALLY-ACTIVE [2]CATENANE MADE TO ORDER
    ASHTON, PR
    IRIEPA, I
    REDDINGTON, MV
    SPENCER, N
    SLAWIN, AMZ
    STODDART, JF
    WILLIAMS, DJ
    TETRAHEDRON LETTERS, 1994, 35 (27) : 4835 - 4838