Enantioselective synthesis of 4-isoxazolines by 1,3-dipolar cycloadditions of nitrones to alkynals catalyzed by fluorodiphenylmethylpyrrolidines

Advanced Synthesis and Catalysis

Volumn 354, Issue 9, 2012, Pages 1665-1671

  Alemán, José ^a   Fraile, Alberto ^a   Marzo, Leyre ^a   Ruano, José Luis García ^a   Izquierdo, Cristina ^a   Díaz Tendero, Sergio ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

2,3 dihydroisoxazoles; 4 isoxazolines; 3+2 cycloaddition reactions; iminium ions; organocatalysis

Indexed keywords

EID: 84862540451     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201200033     Document Type: Article

References (46)

1. T. M. V. D. Pinho e Melo, Eur. J. Org. Chem. 2010, 3363
2. J. P. Freeman, Chem. Rev. 1983, 83, 241
3. P. Grünanger, P. Vita-Finzi, Isoxazolines, in: The Chemistry of Heterocyclic Compounds, (Eds.:, E. C. Taylor, A. Weissberger,), John Wiley & Sons, 1991, Vol. 49, chapter 2, pp 416- 647.
4. A. C. Habeeb, P. N. Praveen Rao, E. E. Knaus, J. Med. Chem. 2001, 44, 2921
5. R. D. Cramer, R. J. Jilek, S. Guessregen, S. J. Clark, B. Wendt, J. Med. Chem. 2004, 47, 6777.
6. M. E. Fraley, R. M. Garbaccio, G. D. Hartman, PCT Int. Appl. WO2006/023440, 43, 2006.
7. J. M. Atienza, D. Susanto, C. Huang, A. S. McCarty, J. Colicelli, J. Biol. Chem. 1999, 274, 4839
8. A. I. Hubich, T. A. Zheldakova, T. V. Chernikhova, E. V. Koroleva, F. A. Lakhvich, M. V. Sholukh, Biochem. Biophys. Res. Commun. 2006, 341, 357.
9. V. Mancuso, C. Hootelé, Tetrahedron Lett. 1988, 29, 5917
10. P. Macours, J. C. Braekman, D. Daloze, Tetrahedron 1995, 51, 1415
11. P. Aschwanden, L. Kærnø, R. W. Geisser, F. Kelinbeck, E. M. Carreira, Org. Lett. 2005, 7, 5741.
12. T. Ishikawa, T. Kudok, J. Yoshida, A. Yashura, S. Manabe, S. Saito, Org. Lett. 2002, 4, 1907
13. N. Wada, K. Kaneko, Y. Ukaji, K. Inomata, Chem. Lett. 2011, 40, 440.
14. A. Sakakura, M. Hori, M. Fushimi, K. Ishihara, J. Am. Chem. Soc. 2010, 132, 15550.
15. Terminal alkynes react with nitrones under copper catalysis affording isoxazolines which in situ evolve into β-lactams, see:, D. A. Evans, F. Kelibeck, M. Rueping, Asymmetric Synthesis-The Essentials, (Eds.:, M. Christmann, S. Braese,), Wiley-VCH, Weinheim, 2007, p 72, and references cited therein.
16. A. M. Gonzáles-Nogal, M. Calle, Tetrahedron 2009, 65, 5472. For tetrasubstituted pyrroles, see
17. S. M. M. Lopes, C. M. Nunes, T. M. V. D. Pinho e Melo, Tetrahedron 2010, 66, 6078
18. A. Liguori, R. Ottana, G. Romeo, G. Sindona, N. Uccella, Tetrahedron 1988, 44, 1247
19. A. Padwa, D. N. Kline, K. F. Koehler, M. Matzinger, M. K. Venkatramanan, J. Org. Chem. 1987, 52, 3909
20. A. Padwa, W. H. Bullock, D. N. Kline, J. Perumattam, J. Org. Chem. 1989, 54, 2862
21. A. Padwa, M. Matzinger, Y. Tomioka, M. K. Venkatramanan, J. Org. Chem. 1988, 53, 955
22. G. Broggini, G. Zecchi, Gazz. Chim. Ital. 1996, 126, 479
23. T. M. V. D. Pinho e Melo, Curr. Org. Chem. 2009, 13, 1406
24. M. Buchlovic, S. Man, K. Kislitsõn, C. Mathot, M. Potácek, Tetrahedron 2010, 66, 1821.
25. D. François, A. Maden, W. V. Murray, Org. Lett. 2004, 6, 1931; from chiral nitrones, see
26. F. Cantagrel, S. Pinet, Y. Gimbert, P. Y. Chavant, Eur. J. Org. Chem. 2005, 2694
27. F. Busqué, P. de March, M. Figueredo, J. Font, T. Gallagher, S. Milán, Tetrahedron: Asymmetry 2002, 13, 437
28. L. Bruché, A. Arnone, P. Bravo, W. Panzeri, C. Pesenti, F. Viani, Eur. J. Org. Chem. 1999, 1665.
29. W. Wei, M. Kobayashi, Y. Ukaji, K. Inomata, Heterocycles 2009, 78, 717.
30. W. S. Jen, J. J. M. Wienr, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874
31. S. S. Chow, M. Navalainen, C. A. Evans, C. W. Johanner, Tetrahedron Lett. 2007, 48, 277
32. S. Karlsson, H.-E. Högberg, Eur. J. Org. Chem. 2003, 2782
33. M. Lemay, J. Trant. W. W. Ogilvie, Tetrahedron 2007, 63, 11644
34. for a general review in 1,3-dipolar reactions, see:, H. Pellissier, Tetrahedron 2007, 63, 3235.
35. X. Cai, C. Wang, J. Sun, Adv. Synth. Catal. 2012, 354, 359-363. For leading references on the activation of alkynals, see
36. S. B. Jones, B. Simmons, D. W. C. MacMillan, J. Am. Chem. Soc. 2009, 131, 13606
37. X. Zhang, S. Zhang, W. Wang, Angew. Chem. 2010, 122, 1523
38. Angew. Chem. Int. Ed. 2010, 49, 1481
39. J. Alemán, A. Núñez, L. Marzo, V. Marcos, C. Alvarado, J. L.García Ruano, Chem. Eur. J. 2010, 16, 9453
40. J. Alemán, C. Alvarado, V. Marcos, A. Nunez, J. L. García Ruano, Synthesis 2011, 1840.
41. For a study iminium ions of α,β-unsaturated aldehydes, see:, C. Sparr, W. B. Schweizer, H. Martín Senn, R. Gilmour, Angew. Chem. 2009, 121, 3111
42. Angew. Chem. Int. Ed. 2009, 48, 3065.
43. M. J. Frisch et al., Gaussian 09 (Revision B.01), Gaussian, Inc., Wallingford CT, 2010.
44. A. D. Becke, J. Chem. Phys. 1993, 98, 1372
45. C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1998, 37, 785.
46. J. Tomasi, B. Mennucci, R. Cammi, Chem. Rev. 2005, 105, 2999.