Highly selective macrocycle formations by metathesis catalysts fixated in nanopores

Journal of Organic Chemistry

Volumn 78, Issue 7, 2013, Pages 3048-3056

  Jee, Joo Eun ^a   Cheong, Jian Liang ^a   Lim, Jaehong ^a   Chen, Cheng ^b   Hong, Soon Hyeok ^b   Lee, Su Seong ^a  

^a INSTITUTE OF BIOENGINEERING AND NANOTECHNOLOGY   (Singapore)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST LOADINGS; IMMOBILIZED CATALYSTS; MACROCYCLE FORMATION; MACROCYCLIC PRODUCTS; MESOCELLULAR SILICEOUS FOAMS; METATHESIS CATALYSTS; RING CLOSING METATHESIS; SUPPORT MATERIALS;

CATALYST SELECTIVITY; NANOPORES; OLIGOMERIZATION; OLIGOMERS; PORE SIZE; REACTION RATES; SILICA;

LOADING;

MACROCYCLIC COMPOUND; RESIN; RUTHENIUM;

ARTICLE; CATALYST; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CYCLIZATION; DENSITY; FOAM; IMMOBILIZATION; MESOCELLULAR SILICEOUS FOAM; NANOPORE; OLIGOMERIZATION; RING CLOSING METATHESIS;

EID: 84875965288     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo302823w     Document Type: Article

References (45)

1. Han, S.-Y.; Chang, S. Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003; Vol. 2, pp 5-127.
2. Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043
3. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527
4. Rivkin, A.; Cho, Y. S.; Gabarda, A. E.; Yoshimura, F.; Danishefsky, S. J. J. Nat. Prod. 2004, 67, 139-143
5. Khan, S. N.; Kim, A.; Grubbs, R. H.; Kwon, Y.-U. Org. Lett. 2011, 13, 1582-1585
6. Nolan, S. P.; Clavier, H. Chem. Soc. Rev. 2010, 39, 3305-3316
7. Gradillas, A.; Perez-Castells, J. Angew. Chem., Int. Ed. 2006, 45, 6086-6101
8. Monfette, S.; Fogg, D. E. Chem. Rev. 2009, 109, 3783-3816
9. Conrad, J. C.; Eelman, M. D.; Silva, J. A. D.; Monfette, S.; Parnas, H. H.; Snelgrove, J. L.; Fogg, D. E. J. Am. Chem. Soc. 2007, 129, 1024-1025
10. Fürstner, A.; Langemann, K. Synthesis 1997, 792-803
11. Hong, S. H.; Wenzel, A. G.; Salguero, T. T.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2007, 129, 7961-7968
12. Hong, S. H.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 7414-7415
13. Badjic, J. D.; Cantrill, S. J.; Grubbs, R. H.; Guidry, E. N.; Orenes, R.; Stoddart, J. F. Angew. Chem., Int. Ed. 2004, 43, 3273-3278
14. Guidry, E. N.; Cantrill, S. J.; Stoddart, J. F.; Grubbs, R. H. Org. Lett. 2005, 7, 2129-2132
15. Hou, H. Y.; Leung, K. C. F.; Lanari, D.; Nelson, A.; Stoddart, J. F.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 15358-15359
16. Clark, P. G.; Guidry, E. N.; Chan, W. Y.; Steinmetz, W. E.; Grubbs, R. H. J. Am. Chem. Soc. 2010, 132, 3405-3412
17. Halbach, T. S.; Mix, S.; Fischer, D.; Maechling, S.; Krause, J. O.; Sievers, C.; Blechert, S.; Nuyken, O.; Buchmeiser, M. R. J. Org. Chem. 2005, 70, 4687-4694
18. Schürer, S. C.; Gessler, S.; Buschmann, N.; Blechert, S. Angew. Chem., Int. Ed. 2000, 39, 3898-3901
19. Mayr, M.; Buchmeiser, M. R.; Wurst, K. Adv. Synth. Catal. 2002, 344, 712-719
20. Prühs, S.; Lehmann, C. W.; Fürstner, A. Organometallics 2004, 23, 280-287
21. Lim, J.; Lee, S. S.; Riduan, S. N.; Ying, J. Y. Adv. Synth. Catal. 2007, 349, 1066-1076
22. Fischer, D.; Blechert, S. Adv. Synth. Catal. 2005, 347, 1329-1332
23. Allen, D. P.; Wingerden, M. M. V.; Grubbs, R. H. Org. Lett. 2009, 11, 1261-1264
24. Vorfalt, T.; Wannowius, K.-J.; Plenio, H. Agew. Chem., Int. Ed. 2010, 49, 5533-5536
25. Vorfalt, T.; Wannowius, K.-J.; Thiel, V.; Plenio, H. Chem.-Eur. J. 2010, 16, 12312-12315
26. Buchmeiser, M. R. Chem. Rev. 2009, 109, 303-321
27. Hagiwara, H.; Nakamura, T.; Okunaka, N.; Hoshi, T.; Suzuki, T. Helv. Chim. Acta 2010, 93, 175-182
28. Coperet, C.; Basset, J. M. Adv. Synth. Catal. 2007, 349, 78-92
29. Grela, K.; Tryznowski, M.; Bieniek, M. Tetrahedron Lett. 2002, 43, 9055-9059
30. Lim, J.; Lee, S. S.; Ying, J. Y. Chem. Commun. 2008, 4312-4314
31. Lim, J.; Lee, S. S.; Ying, J. Y. Chem. Commun. 2010, 46, 806-808
32. Macquarrie, D. H. Ordered Porous Solids: Recent Advances and Prospects; Valtechev, V.; Mintova, S.; Tsapatsis, M., Eds.; Elsevier: New York, 2008; p 725.
33. Molnar, A.; Rac, B. Curr. Org. Chem. 2006, 10, 1697-1726
34. Kidder, M. K.; Britt, P. F.; Zhang, Z. T.; Dai, S.; Hagaman, E. W.; Chaffee, A. L.; Buchanan, A. C. J. Am. Chem. Soc. 2005, 127, 6353-6360
35. Iwamoto, M.; Tanaka, Y.; Sawamura, N.; Namba, S. J. Am. Chem. Soc. 2003, 125, 13032-13033
36. Han, Y.; Lee, S. S.; Ying, J. Y. Chem. Mater. 2007, 19, 2292-2298
37. Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161
38. Courchay, F. C.; Sworen, J. C.; Ghiviriga, I.; Abboud, K. A.; Wagener, K. B. Organometallics 2006, 25, 6074-6086
39. Hadinoto, S.; Lee, S. S.; Ying, J. Y. Adv. Synth. Catal. 2006, 348, 1248-1254
40. Weyl, H. Synthesis of Peptides and Peptidomimetics; Goodman, M.; Felix, A.; Moroder, L.; Toniolo, C., Eds.; Georg Thieme Verlag Stuttgart: New York, 2002; Vol. 22, p 676.
41. Amoroso, D.; Yap, G. P. A.; Fogg, D. E. Organometallics 2002, 21, 3335-3343
42. Amoroso, D.; Snelgrove, J. L.; Conrad, J. C.; Drouin, S. D.; Yap, G. P. A.; Fogg, D. E. Adv. Synth. Catal. 2002, 344, 757-763
43. Litinas, K. E.; Salteris, B. E. J. Chem. Soc., Perkin Trans. 1 1997, 2869-2872
44. Warwel, S.; Tillack, J.; Demes, C.; Kunz, M. Macromol. Chem. Phys. 2001, 202, 1114-1121
45. Fokou, P. A.; Meier, M. A. R. Macromol. Rapid Commun. 2010, 31, 368-373