Synthesis of Inherently Chiral Azacalix[4]arenes and Diazadioxacalix[4]arenes

被引:43
|
作者
Katz, Jeffrey L. [1 ]
Tschaen, Brittany A. [1 ]
机构
[1] Colby Coll, Dept Chem, Waterville, ME 04901 USA
基金
美国国家科学基金会;
关键词
CRYSTAL-STRUCTURE; CAVITY; OXACALIXARENES; COMPLEXATION;
D O I
10.1021/ol1017454
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Described are nucleophilic aromatic substitution reactions for the synthesis of inherently chiral azacalix[4]arenes and diazadioxacalix[4]arenes comprised of two or three different aromatic monomers. A variety of functional groups are tolerated at the 2-, 4-, and 5-positions on the nucleophilic-component monomers; reactions are run under ambient atmosphere; and the macrocycles are constructed without isolation of intermediate linear species.
引用
收藏
页码:4300 / 4303
页数:4
相关论文
共 50 条
  • [21] Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Intramolecular C-H
    Zhang, Yu-Zhen
    Xu, Meng-Meng
    Si, Xu-Ge
    Hou, Jun-Li
    Cai, Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (50) : 22858 - 22864
  • [22] Enzymatic synthesis of nonracemic inherently chiral calix[4]arenes by lipase-catalysed transesterification
    Browne, JK
    McKervey, MA
    Pitarch, M
    Russell, JA
    Millership, JS
    TETRAHEDRON LETTERS, 1998, 39 (13) : 1787 - 1790
  • [23] Design, synthesis and structure determination of new inherently chiral para-bromoalkoxycalix[4]arenes
    Yesypenko, Oleksandr A.
    Klyachina, Marija A.
    Dekhtyarenko, Maksym V.
    Pirozhenko, Vladimir V.
    Shishkina, Svitlana V.
    Boyko, Vyacheslav I.
    Voitenko, Zoia V.
    Kalchenko, Vitaly I.
    SUPRAMOLECULAR CHEMISTRY, 2017, 29 (01) : 49 - 58
  • [24] Cavity-extended inherently chiral resorein[4]arenes: Synthesis and chiroptical properties of the cycloenantiomers
    Paletta, Marlene
    Klaes, Michael
    Neumann, Beate
    Stammler, Hans-Georg
    Grimme, Stefan
    Mattay, Jochen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (03) : 555 - 562
  • [25] Chiral calix[4]arenes
    Okada, Y
    Miao, Z
    Nishimura, J
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (03) : 226 - 235
  • [26] Synthesis of enantiomerically pure inherently chiral calix[4]arenes using the meta-substitution strategy
    Tlusty, Martin
    Spalovska, Dita
    Babor, Martin
    Lhotak, Pavel
    TETRAHEDRON LETTERS, 2019, 60 (03) : 260 - 263
  • [27] Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations
    Yu, Shaoze
    Yuan, Mengyao
    Xie, Wansen
    Ye, Zidan
    Qin, Tianren
    Yu, Na
    Yang, Xiaoyu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (45)
  • [28] First synthesis, isolation and complete characterization of both enantiomers of inherently chiral resorc[4]arenes by monofunctionalization
    Agena, C
    Wolff, C
    Mattay, J
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (15) : 2977 - 2981
  • [29] Catalytic Asymmetric Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations
    Li, Wan
    Shi, Feng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (10) : 3265 - 3267
  • [30] Synthesis and characterization of new chiral calix[4]arenes
    Okada, Y
    Mizutani, M
    Nishimura, J
    ENANTIOMER, 2002, 7 (2-3): : 93 - 106