De novo synthesis of inherently chiral heteracalix[4]aromatics from enantioselective macrocyclization enabled by chiral phosphoric acid-catalyzed intramolecular SNAr reaction

被引:14
作者
Li, Xing-Chi [1 ]
Cheng, Ying [1 ]
Wang, Xu-Dong [2 ]
Tong, Shuo [3 ]
Wang, Mei-Xiang [3 ]
机构
[1] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China
[2] Inst Chem, Chinese Acad Sci, Lab Mol Recognit & Funct, Beijing 100190, Peoples R China
[3] Tsinghua Univ, Dept Chem, MOE Key Lab Bioorgan Phosphorous Chem & Chem Biol, Beijing 100084, Peoples R China
基金
中国国家自然科学基金;
关键词
BRONSTED ACID; CALIXARENES SYNTHESIS; OPTICAL RESOLUTION; CLASSIFICATION;
D O I
10.1039/d3sc06436k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We report herein the synthesis of highly enantiopure inherently chiral N-3,O-calix[2]arene[2]triazines from enantioselective macrocyclization enabled by chiral phosphoric acid-catalyzed intramolecular nucleophilic aromatic substitution reaction. In contrast to documented examples, the inherent chirality of the acquired compounds arises from one heteroatom difference in the linking positions of heteracalix[4](het)arenes.
引用
收藏
页码:3610 / 3615
页数:6
相关论文
共 46 条
  • [1] Enantioselective Mannich-type reaction catalyzed by a chiral Bronsted acid
    Akiyama, T
    Itoh, J
    Yokota, K
    Fuchibe, K
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (12) : 1566 - 1568
  • [2] Recent progress in chiral Bronsted acid catalysis
    Akiyama, Takahiko
    Itoh, Junji
    Fuchibe, Kohei
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) : 999 - 1010
  • [3] Inherently Chiral Calixarenes: Synthesis and Applications
    Arnott, Gareth E.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (08) : 1744 - +
  • [4] INHERENTLY CHIRAL CALIXARENES
    BOHMER, V
    KRAFT, D
    TABATABAI, M
    [J]. JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY, 1994, 19 (1-4): : 17 - 39
  • [5] ASYMMETRICALLY-SUBSTITUTED CALIX(4)ARENES
    BOHMER, V
    MERKEL, L
    KUNZ, U
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) : 896 - 897
  • [6] Enzymatic synthesis of nonracemic inherently chiral calix[4]arenes by lipase-catalysed transesterification
    Browne, JK
    McKervey, MA
    Pitarch, M
    Russell, JA
    Millership, JS
    [J]. TETRAHEDRON LETTERS, 1998, 39 (13) : 1787 - 1790
  • [7] Preparation of both antipodes of enantiopure inherently chiral calix[4]crowns
    Cao, YD
    Luo, J
    Zheng, QY
    Chen, CF
    Wang, MX
    Huang, ZT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) : 206 - 208
  • [8] Casnati A, 2001, CALIXARENES 2001, P365
  • [9] Dalla Cort A, 2004, NEW J CHEM, V28, P1198, DOI 10.1039/b404388j
  • [10] Tetrahomo corona[4]arene-based spirophanes: synthesis, structure, and properties
    Guo, Shen-Yi
    Zhang, Zhuo-Ang
    Tong, Shuo
    Guo, Qing-Hui
    Hua, Ruimao
    Wang, Mei-Xiang
    [J]. CHEMICAL SCIENCE, 2023, 14 (31) : 8393 - 8400