Straightforward synthesis of a double-lasso macrocycle from a nonsymmetrical [c2]daisy chain

Organic Letters

Volumn 15, Issue 1, 2013, Pages 184-187

  Romuald, Camille ^a   Cazals, Guillaume ^b   Enjalbal, Christine ^b   Coutrot, Frédéric ^a  

^a Supramolecular Machines and Architecture Team   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; COPPER; MACROCYCLIC COMPOUND;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; MASS SPECTROMETRY; SYNTHESIS;

ALKYNES; AZIDES; CATALYSIS; COPPER; CYCLIZATION; MACROCYCLIC COMPOUNDS; MASS SPECTROMETRY;

EID: 84874066316     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303186j     Document Type: Article

References (27)

1. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191.
2. Fernandes, A.; Viterisi, A.; Coutrot, F.; Potok, S.; Leigh, D. A.; Aucagne, V.; Papot, S. Angew. Chem., Int. Ed. 2009, 48, 6443-6447.
3. Barnes, J. C.; Fahrenbach, A. C.; Dyar, S. M.; Frasconi, M.; Giesener, M. A.; Zhu, Z.; Liu, Z.; Hartlieb, K. J.; Carmieli, R.; Wasielewski, M. R.; Stoddart, J. F. Proc. Natl. Acad. Sci. U.S.A. 2012, 109, 11446-11551.
4. Ayme, J.-F.; Lux, J.; Sauvage, J.-P.; Sour, A. Chem.-Eur. J. 2012, 18, 5565-5573.
5. Ferrand, Y.; Gan, Q.; Kauffmann, B.; Jiang, H.; Huc, I. Angew. Chem., Int. Ed. 2011, 50, 7572-7575.
6. Gan, Q.; Ferrand, Y.; Bao, C.; Kauffmann, B.; Grelard, A.; Jiang, H.; Huc, I. Science 2011, 331, 1172-1175.
7. Rotzler, J.; Mayor, M. Chem. Soc. Rev. 2013, 42, 44-62.
8. Coutrot, F.; Romuald, C.; Busseron, E. Org. Lett. 2008, 10, 3741-3744.
9. Romuald, C.; Busseron, E.; Coutrot, F. J. Org. Chem. 2010, 75, 6516-6531.
10. Bonnet, S.; Collin, J. P.; Koizumi, M.; Mobian, P.; Sauvage, J. P. Adv. Mater. 2006, 18, 1239-1250.
11. Jimenez-Molero, M. C.; Dietrich-Buchecker, C.; Sauvage, J. P. Chem.-Eur. J. 2002, 8, 1456-1466.
12. Collin, J. P.; Dietrich-Buchecker, C.; Gavina, P.; Jimenez-Molero, M. C.; Sauvage, J. P. Acc. Chem. Res. 2001, 34, 477-487.
13. Consuelo Jimenez, M.; Dietrich-Buchecker, C.; Sauvage, J. P. Angew. Chem., Int. Ed. 2000, 39, 3284-3287.
14. Wu, J.; Leung, K. C. F.; Benitez, D.; Han, J. Y.; Cantrill, S. J.; Fang, L.; Stoddart, J. F. Angew. Chem., Int. Ed. 2008, 47, 7470-7474.
15. Dawson, R. E.; Lincoln, S. F.; Easton, C. J. Chem. Commun. 2008, 3980-3982.
16. Romuald, C.; Arda, A.; Clavel, C.; Jimenez-Barbero, J.; Coutrot, F. Chem. Sci. 2012, 3, 1851-1857.
17. Forgan, R. S.; Sauvage, J.-P.; Stoddart, J. F. Chem. Rev. 2011, 111, 5434-5464.
18. Maksimov, M. O.; Pan, S. J.; Link, A. J. Nat. Prod. Rep. 2012, 29, 996-1006.
19. Huisgen, R. Pure. Appl. Chem. 1989, 61, 613-628.
20. Huisgen, R.; Szeimies, G.; Möbius, L. Chem. Ber. 1967, 100, 2494-2507.
21. Huisgen, R. Angew. Chem. 1963, 75, 604-637.
22. Angew. Chem., Int. Ed. Engl. 1963, 2, 565-598.
23. Huisgen, R. Angew. Chem. 1963, 75, 742-754.
24. Angew. Chem., Int. Ed. Engl. 1963, 2, 633-645.
25. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
26. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
27. Cantrill, S. J.; Youn, G. J.; Stoddart, J. F. J. Org. Chem. 2001, 66, 6857-6872.