Magic ring catenation by olefin metathesis

被引:124
作者
Guidry, EN
Cantrill, SJ
Stoddart, JF
Grubbs, RH
机构
[1] Univ Calif Los Angeles, Calif NanoSyst Inst, Los Angeles, CA 90095 USA
[2] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[3] CALTECH, Arnold & Mabel Beckman Lab Chem Synth, Pasadena, CA 91125 USA
关键词
D O I
10.1021/ol050463f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Olefin metathesis has been employed in the efficient syntheses of a [2]catenane with the templation being provided by the recognition between a secondary ammonium ion and a crown ether. In one approach, a crown ether precursor has been clipped around an NH2+ center situated in a macrocyclic ring, yielding the mechanically interlocked compound. In the other approach, the reversible nature of olefin metathesis allows for a magic ring synthesis to occur wherein two free macrocycles can be employed as the stationary materials, leading to the formation of the same [2]catenane.
引用
收藏
页码:2129 / 2132
页数:4
相关论文
共 60 条
  • [41] 2-2
  • [42] Selection and amplification of hosts from dynamic combinatorial libraries of macrocyclic disulfides
    Otto, S
    Furlan, RLE
    Sanders, JKM
    [J]. SCIENCE, 2002, 297 (5581) : 590 - 593
  • [43] Switching devices based on interlocked molecules
    Pease, AR
    Jeppesen, JO
    Stoddart, JF
    Luo, Y
    Collier, CP
    Heath, JR
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2001, 34 (06) : 433 - 444
  • [44] Rowan SJ, 2002, ANGEW CHEM INT EDIT, V41, P898, DOI 10.1002/1521-3773(20020315)41:6<898::AID-ANIE898>3.0.CO
  • [45] 2-E
  • [46] Thermodynamic synthesis of rotaxanes by imine exchange
    Rowan, SJ
    Stoddart, JF
    [J]. ORGANIC LETTERS, 1999, 1 (12) : 1913 - 1916
  • [47] Structure-directed synthesis under thermodynamic control: Macrocyclic trimers from cinchona alkaloids
    Rowan, SJ
    Brady, PA
    Sanders, JKM
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (18): : 2143 - 2145
  • [48] End-capping of a pseudorotaxane via Diels-Alder reaction for the construction of C60-terminated[2]rotaxanes
    Sasabe, H
    Kihara, N
    Furusho, Y
    Mizuno, K
    Ogawa, A
    Takata, T
    [J]. ORGANIC LETTERS, 2004, 6 (22) : 3957 - 3960
  • [49] Sauvage J.P., 1999, Molecular Catenanes, Rotaxanes and Knots
  • [50] Borromean rings: A one-pot synthesis
    Schalley, CA
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (34) : 4399 - 4401