A study of the scope and regioselectivity of the ruthenium-catalyzed [3 + 2]-cycloaddition of azides with internal alkynes

Journal of Organic Chemistry

Volumn 71, Issue 22, 2006, Pages 8680-8683

  Majireck, Max M ^a   Weinreb, Steven M ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYST ACTIVITY; RUTHENIUM; STEREOCHEMISTRY;

ALKYNES; CYCLOADDITIONS; PROPARGYL ALCOHOLS; REGIOISOMERIC PRODUCTS;

NITROGEN COMPOUNDS;

ACETYLENE DERIVATIVE; ALCOHOL DERIVATIVE; ALKYL GROUP; ALKYNE DERIVATIVE; AMINE; AZIDE; BENZENE DERIVATIVE; RUTHENIUM DERIVATIVE; TRIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

ALKYNES; AZIDES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; RUTHENIUM; STEREOISOMERISM;

EID: 33750473044     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061688m     Document Type: Article

References (27)

1. For reviews of 1,2,3-triazoles, see: (a) Fan, W.-Q.; Katritzky, A. R. In Comprehensive Heterocyclic Chemistry II: Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.: Pergamon Press: Oxford, 1996; Vol. 4, pp 1-126.
2. (b) Dehne, H. In Methoden der Organischen Chemie (Houben-Weyl); Schaumann, E., Ed.; Thieme: Stuttgart, 1994; Vol. E8d, pp 305-405.
3. (c) Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339.
4. For reviews, see: (a) L'Abbe, G. Chem. Rev. 1969, 69, 345.
5. (b) Lwowski, W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New York, 1984; p 559.
6. Sha, C.-K.; Mohanakrishnan, A. K. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Helerocycles and Natural Products; Padwa, A., Pearson, W. H., Eds.; Wiley: New York, 2002; p 623.
7. See for example: (a) Hlasta, D. J.; Ackerman, J. H. J. Org. Chem. 1994, 59, 6184.
8. (b) Coats, S. J.; Link, J. S.; Gauthier, D.; Hlasta, D. J. Org. Lett. 2005, 7, 1469.
9. Li, Z.; Seo, T. S.; Ju, J. Tetrahedron Lett. 2004, 45, 3143.
10. For reviews of "click chemistry", see: (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
11. (b) Bock, V. D.; Hiemstra, H.; van Maarseveen, J. H. Eur. J. Org. Chem. 2006, 51.
12. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
13. (b) Himo, F.; Lovell, T.; Hilgraf, R.; Rostovtsev, V. V.; Noodleman, L.; Sharpless, K. B.; Fokin, V. V. J. Am. Chem. Soc. 2005, 127, 210.
14. Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853.
15. For recent improved experimental procedures, see: (a) Lee, B.-Y.; Park, S. R.; Jeon, H. B.; Kim, K. S. Tetrahedron Lett. 2006, 47, 5105.
16. (b) Reddy, K. R.; Rajgopal, K.; Kantam, M. L. Synlett 2006, 957.
17. Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
18. Zhang, L.; Chen, X.; Xue, P.; Sun, H. H. Y.; Williams, I. D.; Sharpless, K. B.; Fokin, V. V.; Jia, G. J. Am. Chem. Soc. 2005, 127, 15998.
19. Yap, A. H.; Weinreb, S. M. Tetrahedron Lett. 2006, 47, 3035.
20. See for example: Na, Y.; Chang, S. Org. Lett. 2000, 2, 1887.
21. Demko, Z. P.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2110.
22. (a) Olsen, C. E. Acta Chem. Scand. 1973, 27, 2983.
23. (b) Olsen, C. E. Acta Chem. Scand. B 1975, 29, 953.
24. Cottrell, I. F.; Hands, D.; Houghton, P. G.; Humphrey, G. R.; Wright, S. H. B. J. Heterocycl. Chem. 1991, 28, 301.
25. (a) Prager, R. H.; Razzino, P. Aust. J. Chem. 1994, 47, 1375.
26. (b) Cwiklicki, A.; Rehse, K. Arch. Pharm. Pharm. Med. Chem. 2004, 337, 156.
27. Wu, Y.-M.; Deng, J.; Li, Y.; Chen, Q.-Y. Synthesis 2005, 8, 1314.