Microwave-assisted domino access to C 2-chain functionalized furans from tertiary propargyl vinyl ethers

Organic Letters

Volumn 13, Issue 16, 2011, Pages 4422-4425

  Tejedor, David ^a,b   Cotos, Leandro ^a   García Tellado, Fernando ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b Madrid Spain   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; VINYL DERIVATIVE; VINYL ETHER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MICROWAVE RADIATION; SYNTHESIS;

FURANS; MICROWAVES; MOLECULAR STRUCTURE; VINYL COMPOUNDS;

EID: 80051683263     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2017609     Document Type: Article

References (38)

1. Sherry, B. D.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 15978
2. Hashmi, A. S. K. Synthesis of Allenes by Isomerization Reactions in Modern Allene Chemistry; Krause, N.; Hashmi, A. S. K., Eds.; Wiley-VCH: Weinheim, Germany, 2004.
3. Gille, A.; Rehbein, J.; Hiersemann, M. Org. Lett. 2011, 13, 2122
4. Jiang, H.; Yao, W.; Cao, H.; Huang, H.; Cao, D. J. Org. Chem. 2010, 75, 5347
5. Cao, H.; Jiang, H.; Mai, R.; Zhu, S.; Qi, C. Adv. Synth. Catal. 2010, 352, 143
6. Cao, H.; Jiang, H.; Yao, W.; Liu, X. Org. Lett. 2009, 11, 1931
7. Suhre, M. H.; Reif, M.; Kirsch, S. F. Org. Lett. 2005, 7, 3925
8. Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151
9. Menz, H.; Kirsch, S. F. Org. Lett. 2006, 8, 4795
10. Sherry, D.; Maus, L.; Laforteza, B. N. F.; Toste, D. J. Am. Chem. Soc. 2006, 128, 8132
11. Wei, H.; Wang, Y.; Yue, B.; Xu, P.-F. Adv. Synth. Catal. 2010, 352, 245
12. Harschneck, T.; Kirsch, S. F. J. Org. Chem. 2011, 76, 2145
13. Tejedor, D.; Méndez-Abt, G.; Cotos, L.; Ramirez, M. A.; García-Tellado, F. Chem.-Eur. J. 2011, 17, 3318
14. Tejedor, D.; Méndez-Abt, G.; García-Tellado, F. Chem.-Eur. J. 2010, 16, 6582
15. Tejedor, D.; Méndez-Abt, G.; García-Tellado, F. Eur. J. Org. Chem. 2010, 6582
16. ABB′ 3CRs refers to a three-component reaction that utilizes two different components (A and B) to give a product which incorporates into its structure one unit of component A and two chemo-differentiated units of component B (B and B′). For full details and more examples of this type of multicomponent reactions, see: Tejedor, D.; García-Tellado, F. Chem. Soc. Rev. 2007, 36, 484
17. Tejedor, D.; Santos-Expósito, A.; García-Tellado, F. Chem.-Eur. J. 2007, 13, 1201
18. Tejedor, D.; Santos-Expósito, A.; Méndez-Abt, G.; Ruiz-Pérez, C.; García-Tellado, F. Synlett 2009, 1223
19. Inanaga, J.; Baba, Y.; Hanamoto, T. Chem. Lett. 1993, 241
20. Kirsch, S. F. Synthesis 2008, 3183
21. D'Souza, D. M.; Müller, T. J. J. Chem. Soc. Rev. 2007, 36, 1095
22. Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076
23. Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850
24. Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536 and references cited therein
25. Albrecht, L.; Ransborg, L. K.; Gschwend, B.; Jorgensen, K. A. J. Am. Chem. Soc. 2010, 132, 17886
26. Hashmi, A. S. K.; Lothar Schwarz, L.; Choi, J.-H.; Frost, T. M. Angew. Chem., Int. Ed. 2000, 39, 2285
27. Hou, X. L.; Yang, Z.; Yeung, K.-S.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A., Eds.; Pergamon: Oxford, 2008; Vol. 19, p 176.
28. Balme, G.; Bouyssi, D.; Monteiro, N. Heterocycles 2007, 73, 87
29. Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Gilchrist, T. L., Eds.; Pergamon: Oxford, 2003; Vol. 15.
30. Keay, B. A.; Dibble, P. W. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Elsevier: Oxford, 1997; Vol. 2.
31. Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 4.
32. Mortensen, D. S.; Rodriguez, A. L.; Carlson, K. E.; Sun, J.; Katzenellenbogen, B. S.; Katzenellenbogen, J. A. J. Med. Chem. 2001, 44, 3838
33. Francesconi, I.; Wilson, W. D.; Tanious, F. A.; Hall, J. E.; Bender, B. C.; Tidwell, R. R.; McCurdy, D.; Boykin, D. W. J. Med. Chem. 1999, 42, 2260
34. Rahmathullah, S. M.; Hall, J. E.; Bender, B. C.; McCurdy, D. R.; Tidwell, R. R.; Boykin, D. W. J. Med. Chem. 1999, 42, 3994
35. Zhang, L. Z.; Chen, C. W.; Lee, C. F.; Wu, C. C.; Luh, T. Y. Chem.Commun. 2002, 2336
36. Tejedor, D.; González-Cruz, D.; García-Tellado, F.; Marrero-Tellado, J. J.; Rodriguez, M. L. J. Am. Chem. Soc. 2004, 126, 8390
37. The triethylamine-catalyzed reaction of methyl propiolate and unbranched aliphatic 1,2-ketoesters affords the corresponding isotetronic acid derivatives via an enolate-driven domino ABB′ 3CR. For more details, see: Tejedor, D.; Santos-Expósito, A.; García-Tellado, F. Chem. Commun. 2006, 2667
38. Lithium acetylides were prepared according the standard procedure. See: Nielsen, T. E.; Tanner, D. J. Org. Chem. 2002, 67, 6366