1,3-dipolar cycloaddition of hydrazones with α-oxo-ketenes: A three-component stereoselective entry to pyrazolidinones and an original class of spirooxindoles

Organic Letters

Volumn 13, Issue 15, 2011, Pages 4124-4127

  Presset, Marc ^a   Mohanan, Kishor ^a   Hamann, Marie ^a   Coquerel, Yoann ^a   Rodriguez, Jean ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79961037695     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2016669     Document Type: Article

References (47)

1. For efforts to clarify the terminologies of MBFTs, see: Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. 1993, 32, 131
2. Tietze, L. F. Chem. Rev. 1996, 96, 115
3. Tietze, L. F.; Brasche, G.; Gericke, K. M. Domino Reactions in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
4. Multicomponent Reactions; Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
5. Coquerel, Y.; Boddaert, T.; Presset, M.; Mailhol, D.; Rodriguez, J. In Ideas in Chemistry and Molecular Sciences: Advances in Synthetic Chemistry; Pignataro, B., Ed.; Wiley-VCH: Weinheim, Germany, 2010; Chapter 9, p 187.
6. Selected recent reviews: Kruithof, A.; Ruijter, E.; Orru, R. V. A. Curr. Org. Chem. 2011, 15, 204
7. Bonne, D.; Coquerel, Y.; Constantieux, T.; Rodriguez, J. Tetrahedron: Asymmetry 2010, 21, 1085
8. Jiang, B.; Rajale, T.; Wever, W.; Tu, S.-J.; Li, G. Chem.-Asian. J. 2010, 5, 2318
9. Dolle, R. E.; Le Bourdonnec, B.; Worm, K.; Morales, G. A.; Thomas, C. J.; Zhang, W. J. Comb. Chem. 2010, 12, 765
10. Estevez, V.; Villacampa, M.; Menéndez, J. C. Chem. Soc. Rev. 2010, 39, 4402
11. Reviews: Claramunt, R. M.; Elguero, J. Org. Prep. Proced. Int. 1991, 23, 273
12. Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789 For organocatalytic properties, see: Gould, E.; Lebl, T.; Slawin, A. M. Z.; Reid, M.; Smith, A. D. Tetrahedron 2010, 66, 8992 and references therein
13. Reviews: Wentrup, C.; Heilmayer, W.; Kollenz, G. Synthesis 1994, 1219
14. Kollenz, G.; Ebner, S. In Science of Synthesis: Houben-Weyl methods of molecular transformations; Danheiser, R., Ed.; Georg Thieme Verlag: Stuttgart, Germany, 2006; Vol. 23, Chapter 9, p 271.
15. Reber, K. P.; Tilley, S. D.; Sorensen, E. J. Chem. Soc. Rev. 2009, 38, 3022
16. For recent examples from our laboratory, see: Presset, M.; Coquerel, Y.; Rodriguez, J. J. Org. Chem. 2009, 74, 415
17. Presset, M.; Coquerel, Y.; Rodriguez, J. Org. Lett. 2009, 11, 5706
18. Presset, M.; Coquerel, Y.; Rodriguez, J. Org. Lett. 2010, 12, 4212
19. Grigg, R.; Kemp, J.; Thompson, N. Tetrahedron Lett. 1978, 19, 2827
20. Le Fevre, G.; Hamelin, J. Tetrahedron Lett. 1978, 19, 4503
21. Arrieta, A.; Carrillo, J. R.; Cossio, F. P.; Díaz-Ortiz, A.; Gómez-Escalonilla, M. J.; de la Hoz, A.; Langa, F.; Moreno, A. Tetrahedron 1998, 54, 13167
22. For an authoritative review, see: Kirmse, W. Eur. J. Org. Chem. 2002, 2193
23. CCDC 800272 (6h), 800274 (6i), and 800273 (10a) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via the Internet from The Cambridge Crystallographic Data Centre at www.ccdc.cam.ac.uk/data-request/cif or from the publisher's website at http://pubs.acs.org.
24. Quaternary Stereocenters: Challenges and Solutions for Organic Synthesis; Christoffers, J.; Baro, A., Eds.; Wiley-VCH: Weinheim, Germany, 2005.
25. For examples of [4 + 2] cycloadditions between α-oxo-ketenes and hydrazono compounds, see: Pulina, N. A.; Zalesov, V. V.; Glebova, E. A. Chem. Heterocycl. Compd. 2002, 38, 1289 For examples of [2 + 4] cycloadditions of α,β-unsaturated hydrazones, see: Waldner, A. Helv. Chim. Acta 1989, 72, 1435
26. Reviews: Marti, C.; Carreira, E. M. Eur. J. Org. Chem. 2003, 2209
27. Galliford, C. V.; Scheidt, K. A. Angew. Chem., Int. Ed. 2007, 46, 8748
28. Trost, B. M.; Brennan, M. K. Synthesis 2009, 3003
29. Peddibhotla, S. Curr. Bioact. Compd. 2009, 5, 20
30. Zhou, F.; Liu, Y.-L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381
31. For discussions, see: Wilson, R. M.; Danishefsky, S. J. J. Org. Chem. 2006, 71, 8329
32. Cordier, C.; Morton, D.; Murrison, S.; Nelson, A.; O'Leary-Steele, C. Nat. Prod. Rep. 2008, 25, 719
33. Wender, P. A.; Verma, V. A.; Paxton, T. J.; Pillow, T. H. Acc. Chem. Res. 2008, 41, 40
34. Kumar, K.; Waldmann, H. Angew. Chem., Int. Ed. 2009, 48, 3224
35. Najera, C.; Sansano, J. M. Curr. Org. Chem. 2003, 7, 1105
36. Eberbach, W. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Padwa, A., Ed.; Georg Thieme Verlag: Stuttgart, 2004; Vol. 27, Chapter 11, p 441.
37. For representative approaches to type 7 spirooxindoles, see: Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666
38. Lo, M. M.-C.; Neumann, C. S.; Nagayama, S.; Perlstein, E. O.; Schreiber, S. L. J. Am. Chem. Soc. 2004, 126, 16077
39. Chen, X.-H.; Wei, Q.; Luo, S.-W.; Xiao, H.; Gong, L.-Z. J. Am. Chem. Soc. 2009, 131, 13819 For recent representative approaches to type 8 spirooxindoles, see: Karthikeyan, K.; Sivakumar, P. M.; Doble, M.; Perumal, P. T. Eur. J. Med. Chem. 2010, 45, 3446
40. Ghandi, M.; Taheri, A.; Abbasi, A. Tetrahedron 2010, 66, 6744
41. Liu, H.; Dou, G.; Shi, D. J. Comb. Chem. 2010, 12, 633
42. Kumar, R. S.; Rajesh, S. M.; Perumal, S.; Banerjee, D.; Yogeeswari, P.; Sriram, D. Eur. J. Med. Chem. 2010, 45, 411
43. Karthikeyan, S. V.; Bala, B. D.; Raja, V. P. A.; Perumal, S.; Yogeeswari, P.; Sriram, D. Bioorg. Med. Chem. Lett. 2010, 20, 350
44. Zhao, K.; Zhu, S.-L.; Shi, D.-Q.; Xu, X.-P.; Ji, S.-J. Synthesis 2010, 1793
45. For conceptually distinct approaches of limited scope to type 10 spirooxindoles based on hydrazinolysis of 3-alkylidene oxindoles, see for example: Hasaninejad, A.; Zare, A.; Shekouhy, M. Tetrahedron 2011, 67, 390
46. Shanthi, G.; Perumal, P. T. J. Chem. Sci. 2010, 122, 415
47. Gabr, Y.; Abdel-Megid, M.; Abdel-Hamid Awas, M.; Abdel-Fatah, N. M. Heterocycles 2010, 81, 395 For another approach of very limited breadth involving isatin hydrazone, see: Ganoub, N. A. Heterocycl. Commun. 2001, 7, 143