A dual gold-Iron catalysis for a one-Pot synthesis of 2,3-Dihydroisoxazoles from propargylic alcohols and N-Protected hydroxylamines

Advanced Synthesis and Catalysis

Volumn 351, Issue 11-12, 2009, Pages 1991-1998

  Debleds, Olivier ^a   Zotto, Christophe Dal ^a   Vrancken, Emmanuel ^a   Campagne, Jean Marc ^a   Retailleau, Pascal ^b  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

Gold; Heterocycles; Homogeneous catalysis; Iron

Indexed keywords

EID: 68949150953     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200900127     Document Type: Article

References (43)

1. a) A. G. Habeeb, P. N.Praveen Rao, E. E. Knaus, J. Med. Chem. 2001, 44, 2921-2927;
2. b) M. E. Fraley, R. M. Garbaccio, G. D. Hartman, Patent WO 2006023440, 2006.
3. T. Ishikawa, T. Kudoh, J. Yoshida, A. Yasuhara, S. Manabe, S. Saito, Org. Lett. 2002, 4, 1907-1910.
4. a) J. P. Freeman, Chem. Rev. 1983, 83, 241-261;
5. b) D. Gonzalez-Cruz, D. Tejedo, P. de Armas, F. Garcia-Tellado, Chem. Eur. J 2007, 13, 4823-4832.
6. M. Fabio, L. Ronzini, L. Troisi, Tetrahedron 2008, 64, 4979-4984.
7. P. Aschwanden, D. E. Frantz, E. M. Carreira, Org. Lett. 2000, 2, 2331-2333.
8. a) M. Georgy, V. Boucard, J.-M. Campagne, J. Am. Chem. Soc. 2005, 127, 14180-14181;
9. b) M. Georgy, V. Boucard, O. Debleds, C. D. Zotto, J.-M. Campagne, Tetrahedron 2009, 65, 1758-1766.
10. a) For a gold(I) catalyzed hydroaminative cyclization leading to 2,5-dihydroisoxazole, see: H. K. Yeom, E. S. Lee, S. Shin, Synlett 2007, 2292-2294;
11. b) for a one-pot gold(III)-catalyzed synthesis of isoxazoles from alkynes and nitric acid, see: F. Gasparini, M. Giovannoli, D. Misiti, G. Natile, G. Palmieri, L. Maresca, J. Am. Chem. Soc. 1993, 115, 4401-4402.
12. For recent reviews, see: a) G. W. Kabalka, M.-L. Yao, Curr. Org. Synth. 2008, 5, 28-32;
13. b) N. Ljungdahl, N. Kann, Angew. Chem. 2009, 121, 652-654;
14. Angew. Chem. Int. Ed. 2009, 48, 642-644; for some selected recent papers, see:
15. c) R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriguez, Eur. J. Org. Chem. 2006, 1383-1386;
16. d) X.-T. Liu, L. Huang, F.-J. Zheng, Z.-P. Zhan, Adv. Synth. Catal. 2008, 350, 2778-2788;
17. e) H. Qin, N. Yamagiwa, S. Matsunaga, M. Shibasaki, Angew. Chem. 2007, 119, 413-417;
18. Angew. Chem. Int. Ed. 2007, 46, 409-413.
19. Z.-P. Zhan, J.-L. Yu, H.-J. Liu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem. 2006, 71, 8298-8301.
20. For recents reviews, see : a) C. Bolm, J. Legros, J. Le Paih, L. Zani, Chem. Rev. 2004, 104, 6217-6254;
21. b) B. D. Sherry, A. Fürstner, Acc. Chem. Res. 2008, 41, 1500-1511;
22. c) A. Correa, O. Garcia Mancheno, C. Bolm, Chem. Soc. Rev. 2008, 37, 1108-1117;
23. d) S. Enthaler, K. Junge, M. Beller, Angew. Chem. 2008, 120, 3363-3367;
24. Angew. Chem. Int. Ed. 2008, 47, 3317-3321.
25. For iron-catalyzed reactions from these laboratories, see: a) J. Michaux, V. Terrasson, S. Marque, J. Wehbe, D. Prim, J.-M. Campagne, Eur. J. Org. Chem. 2007, 2601-2603;
26. b) C. Dal Zotto, J. Wehbe, D. Virieux, J.-M. Campagne, Synlett 2008, 2033-2035;
27. c) C. Dal Zotto, D. Virieux, J.-M. Campagne, Synlett 2009, 276-278.
28. For successful related gold-catalyzed cyclization of homopropargylic alcohols, see: a) S. Antoniotti, E. Genin, V. Michelet, J.-P. Genet, J. Am. Chem. Soc. 2005, 127, 9976-9977;
29. b) V. Belting, N. Krause, Org. Lett. 2006, 8, 4489-4492. For general reviews on this topic, see:
30. c) A. S. K. Hashmi, G. J Hutchings, Angew. Chem. 2006, 118, 8064-8105;
31. Angew. Chem. Int. Ed. 2006, 45, 7896-7936;
32. d) J. Muzart, Tetrahedron 2008, 64, 5815-5849.
33. [5]), cyclizations of N-alkyl-protected hydroxylamines are described.
34. Thanks to a referee for suggesting this control experiment.
35. V. Terrasson, S. Marque, M. Georgy, J.-M. Campagne, D. Prim, Adv. Synth. Catal. 2006, 348, 2063-2067.
36. A 'hydration' pathway can also be postulated to account for the formation of 5ab from 3ab [Scheme 6, Eq. (b)], through the formation of compound 6 (Scheme 7, path A2).
37. For the successful use of pyridine ligands in gold(III) catalysis: A. S. K. Hashmi, J. P. Weyrauch, M. Rudolph, E. Kurpejovic, Angew. Chem. 2004, 116, 6707-6709;
38. Ang. Chem. Int. Ed 2004, 43, 6545-6547.
39. a) R. S. Ramon, N. Marion, S. P. Nolan, Tetrahedron 2009, 65, 1767-1773;
40. b) N. Marion, P. Carlquist, R. Gealageas, P. de Fremont, F. Maseras, S. P. Nolan, Chem. Eur. J. 2007, 13, 6437-6451.
41. For previously observed different selectivities between gold and other Lewis acids, see: J. Liu, E. Muth, U. Floerke, G. Henkel, K. Merz, J. Sauvageau, E. Schwake, G. Dyker, Adv. Synth. Catal. 2006, 348, 456-462.
42. a) J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302-312;
43. b) J.-C. Wasilke, S. J. Obrey, R. T. Baker, G. C. Bazan, Chem. Rev. 2005, 105, 1001-1020.