Design of a novel inherently chiral calix[4]arene for chiral molecular recognition

被引：98
|
作者：
Shirakawa, Seiji
Moriyama, Akihiro
Shimizu, Shoichi [1 ]
机构：
[1] Nihon Univ, Coll Ind Technol, Dept Appl Mol Chem, Narashino, Chiba 2758575, Japan
[2] Nihon Univ, Coll Ind Technol, High Technol Res Ctr, Narashino, Chiba 2758575, Japan
来源：
ORGANIC LETTERS | 2007年 / 9卷 / 16期
关键词：
D O I：
10.1021/ol071249p
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[GRAPHICS] A newly designed inherently chiral calix[4]arene was synthesized and resolved to an optically pure form. Enantiomeric recognition ability of the chiral calix[4]arene was examined using H-1 NMR experiments with mandelic acid. In addition, the chiral calix[4]arene was applied to asymmetric reactions, as an organocatalyst.
引用
下载
收藏
页码：3117 / 3119
页数：3
相关论文
共 50 条
  • [41] Synthesis and enantiorecognition properties of stereoisomeres of inherently chiral propyloxy-octyloxy-calix[4]arene acetic acids
    Yesypenko, Oleksandr A.
    Osipova, Anastasia O.
    Tribrat, Oleksandr O.
    Kravchenko, Sergii O.
    Usachov, Oleg M.
    Dyakonenko, Viktoriya V.
    Ryabitskii, Aleksey B.
    Pirozhenko, Vladimir V.
    Shishkina, Svitlana, V
    Rozhenko, Alexander B.
    Kalchenko, Vitaly, I
    TETRAHEDRON, 2021, 80
  • [42] One-shot preparation of an inherently chiral trifunctional calix[4]arene from an easily available cone-triformylcalix[4]arene
    Ciaccia, Maria
    Tosi, Irene
    Cacciapaglia, Roberta
    Casnati, Alessandro
    Baldini, Laura
    Di Stefano, Stefano
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (22) : 3642 - 3648
  • [43] 25-Propyloxy-26,27-dibenzoyloxy-calix[4]arene as Precursor for the Synthesis of Inherently Chiral Calixarenes
    Trybrat, Oleksandr O.
    Yesypenko, Oleksandr A.
    Shishkina, Svitlana, V
    Rusanov, Eduard B.
    Karpichev, Yevgen A.
    Kalchenko, Vitaly, I
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (28) : 3912 - 3919
  • [44] Diastereoselective lower rim (1S)-camphorsulfonylation as the shortest way to the inherently chiral calix[4]arene
    Yakovenko, Anton V.
    Boyko, Vyacheslav I.
    Danylyuk, Oksana
    Suwinska, Kinga
    Lipkowski, Janusz
    Kalchenko, Vitaly I.
    ORGANIC LETTERS, 2007, 9 (07) : 1183 - 1185
  • [45] Synthesis of an Inherently Chiral Calix[4]arene Amino Acid and Its Derivatives: Their Application to Asymmetric Reactions as Organocatalysts
    Shirakawa, Seiji
    Shimizu, Shoichi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) : 1916 - 1924
  • [46] Synthesis and structures of novel enantiopure inherently chiral calix[4]arene-derived salphen ligands and their transition-metal complexes
    Xu, Zhen-Xiang
    Huang, Zhi-Tang
    Chen, Chuan-Feng
    TETRAHEDRON LETTERS, 2009, 50 (38) : 5430 - 5433
  • [47] Selective nitration of calix[4]arenes that easily gave inherently chiral calix[4]arenes
    Jin-Hua Wang
    Yi-Chang Chen
    Yan-Song Zheng
    Chang-Hong Shen
    Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2014, 80 : 449 - 455
  • [48] Selective nitration of calix[4]arenes that easily gave inherently chiral calix[4]arenes
    Wang, Jin-Hua
    Chen, Yi-Chang
    Zheng, Yan-Song
    Shen, Chang-Hong
    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2014, 80 (3-4) : 449 - 455
  • [49] Inherently chiral derivatives of calix[5]crowns
    Arnecke, R
    Bohmer, V
    Ferguson, G
    Pappalardo, S
    TETRAHEDRON LETTERS, 1996, 37 (09) : 1497 - 1500
  • [50] Ketone transformation as a pathway to inherently chiral rigidified calix[4]arenes
    Tlusty, Martin
    Spalovska, Dita
    Kohout, Michal
    Eigner, Vaclav
    Lhotak, Pavel
    CHEMICAL COMMUNICATIONS, 2020, 56 (84) : 12773 - 12776
12345