A Rotaxane-Based Switchable Organocatalyst

被引:216
作者
Blanco, Victor [1 ]
Carlone, Armando [1 ]
Haenni, Kevin D. [1 ]
Leigh, David A. [1 ,2 ]
Lewandowski, Bartosz [1 ]
机构
[1] Univ Edinburgh, Sch Chem, Edinburgh EH9 3JJ, Midlothian, Scotland
[2] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
Michael addition; molecular machines; molecular switches; organocatalysis; rotaxanes; MOLECULAR MACHINE; TRANSLATIONAL ISOMERISM; TRIAZOLIUM STATION; TERMINAL ALKYNES; LOGIC GATES; SHUTTLE; PROPEPTIDES; CHEMISTRY; CATALYSIS; AZIDES;
D O I
10.1002/anie.201201364
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Switch it on! The activity of an organocatalytic group incorporated within a rotaxane architecture can be controlled by switching the position of the macrocycle. The system was used to mediate the progress of the Michael addition of an aliphatic thiol to trans-cinnamaldehyde. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:5166 / 5169
页数:4
相关论文
共 63 条
[11]   A new pH-switchable dimannosyl[c2]daisy chain molecular machine [J].
Coutrot, Frederic ;
Romuald, Camille ;
Busseron, Eric .
ORGANIC LETTERS, 2008, 10 (17) :3741-3744
[12]   A new glycorotaxane molecular machine based on an anilinium and a triazolium station [J].
Coutrot, Frederic ;
Busseron, Eric .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (16) :4784-4787
[13]   Iminium catalysis [J].
Erkkila, Anniina ;
Majander, Inkeri ;
Pihko, Petri M. .
CHEMICAL REVIEWS, 2007, 107 (12) :5416-5470
[14]  
Fernandes A., 2009, ANGEW CHEM, V121, P6565
[15]   Rotaxane-Based Propeptides: Protection and Enzymatic Release of a Bioactive Pentapeptide [J].
Fernandes, Anthony ;
Viterisi, Aurelien ;
Coutrot, Frederic ;
Potok, Stephanie ;
Leigh, David A. ;
Aucagne, Vincent ;
Papot, Sebastien .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (35) :6443-6447
[16]   Second generation specific-enzyme-activated rotaxane propeptides [J].
Fernandes, Antony ;
Viterisi, Aurelien ;
Aucagne, Vincent ;
Leigh, David A. ;
Papot, Sebastien .
CHEMICAL COMMUNICATIONS, 2012, 48 (15) :2083-2085
[17]   Light-Operated Mechanized Nanoparticles [J].
Ferris, Daniel P. ;
Zhao, Yan-Li ;
Khashab, Niveen M. ;
Khatib, Hussam A. ;
Stoddart, J. Fraser ;
Zink, Jeffrey I. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (05) :1686-+
[18]   Squaraine Rotaxane as a Reversible Optical Chloride Sensor [J].
Gassensmith, Jeremiah J. ;
Matthys, Sarah ;
Lee, Jung-Jae ;
Wojcik, Aleksandra ;
Kamat, Prashant V. ;
Smith, Bradley D. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (09) :2916-2921
[19]  
Ge Z., 2009, ANGEW CHEM, V121, P1830, DOI DOI 10.1002/ANGE.200805712
[20]   Responsive Supramolecular Gels Constructed by Crown Ether Based Molecular Recognition [J].
Ge, Zhishen ;
Hu, Jinming ;
Huang, Feihe ;
Liu, Shiyong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (10) :1798-1802