A Switchable [2]Rotaxane Asymmetric Organocatalyst That Utilizes an Acyclic Chiral Secondary Amine

被引:171
作者
Blanco, Victor [1 ]
Leigh, David A. [1 ]
Marcos, Vanesa [1 ]
Morales-Serna, Jose A. [1 ]
Nussbaumer, Alina L. [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
瑞士国家科学基金会; 英国工程与自然科学研究理事会;
关键词
ALPHA; BETA-UNSATURATED ALDEHYDES; MICHAEL ADDITION; CATALYSIS; ROTAXANE; LIGHT; AMINOCATALYSIS; NANOSWITCH; 3-STATION; STATION; ADVENT;
D O I
10.1021/ja501561c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A rotaxane-based switchable asymmetric organocatalyst has been synthesized in which the change of the position of the macrocycle reveals or conceals an acyclic, yet still highly effective, chiral organocatalytic group. This allows control over both the rate and stereochemical outcome of a catalyzed asymmetric Michael addition.
引用
收藏
页码:4905 / 4908
页数:4
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共 67 条
  • [1] Hydrogen-Bonding in Aminocatalysis: From Proline and Beyond
    Albrecht, Lukasz
    Jiang, Hao
    Jorgensen, Karl Anker
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (02) : 358 - 368
  • [2] Applications of asymmetric organocatalysis in medicinal chemistry
    Aleman, Jose
    Cabrera, Silvia
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) : 774 - 793
  • [3] Influence of the Reaction Conditions on the Evolution of the Michael Addition of β-Keto Sulfones to α,β-Unsaturated Aldehydes
    Aleman, Jose
    Marcos, Vanesa
    Marzo, Leyre
    Garcia Ruano, Jose Luis
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (23) : 4482 - 4491
  • [4] Organocatalytic asymmetric conjugate additions
    Almasi, Diana
    Alonso, Diego A.
    Najera, Carmen
    [J]. TETRAHEDRON-ASYMMETRY, 2007, 18 (03) : 299 - 365
  • [5] First asymmetric cascade reaction catalysed by chiral primary aminoalcohols
    Arroniz, Carlos
    Escolano, Carmen
    Luque, F. Javier
    Bosch, Joan
    Amat, Mercedes
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (14) : 5079 - 5085
  • [6] Switchable Catalysis with a Light-Responsive Cavitand
    Berryman, Orion B.
    Sather, Aaron C.
    Lledo, Agusti
    Rebek, Julius, Jr.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (40) : 9400 - 9403
  • [7] Organocatalysis-after the gold rush
    Bertelsen, Soren
    Jorgensen, Karl Anker
    [J]. CHEMICAL SOCIETY REVIEWS, 2009, 38 (08) : 2178 - 2189
  • [8] A Rotaxane-Based Switchable Organocatalyst
    Blanco, Victor
    Carlone, Armando
    Haenni, Kevin D.
    Leigh, David A.
    Lewandowski, Bartosz
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) : 5166 - 5169
  • [9] Organocatalytic conjugate addition of malonates to α,β-unsaturated aldehydes:: Asymmetric formal synthesis of (-)-paroxetine, chiral lactams, and lactones
    Brandau, Sven
    Landa, Aitor
    Franzen, Johan
    Marigo, Mauro
    Jorgensen, Karl Anker
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (26) : 4305 - 4309
  • [10] N-Benzyltriazolium as Both Molecular Station and Barrier in [2]Rotaxane Molecular Machines
    Busseron, Eric
    Coutrot, Frederic
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (08) : 4099 - 4106