Unprecedented base-promoted nucleophilic addition of diazoesters to nitrones

Tetrahedron Letters

Volumn 54, Issue 37, 2013, Pages 5103-5105

  Lieou Kui, Evelyn ^a   Kanazawa, Alice ^a   Poisson, Jean François ^a   Py, Sandrine ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

Diazoesters; Hydroxylamines; Nitrones; Nucleophilic addition; Sugar derived nitrones

Indexed keywords

ESTER; HYDROXYLAMINE; NITRONE; SOLVENT; SUGAR;

ARTICLE; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; NUCLEOPHILICITY;

EID: 84881135643     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.044     Document Type: Article

References (69)

1. For reviews, see: P. Merino, and T. Tejero Molecules 4 1999 169 179
2. M. Lombardo, and C. Trombini Synthesis 2000 759 774
3. P. Merino Compounds with two carbon-heteroatom bonds: Heteroatom analogues of aldehydes and ketones A. Padwa, D. Bellus, Science of Synthesis 2004 Stuttgard Georg Thieme Verlag 511 580
4. P.C.R. Merino Chimie 8 2005 775 788
5. J. Revuelta, S. Cichi, A. Goti, and A. Brandi Synthesis 2007 485 504
6. P. Merino, and T. Tejero Synlett 2011 1965 1977
7. J. Yang Synlett 23 2012 2293 2297
8. M. Frederickson Tetrahedron 53 1997 403 425
9. K.V. Gothelf, and K.A. Jorgensen Chem. Rev. 98 1998 863 909
10. A. Padwa Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products W.H. Pearson, 2002 John Wiley Sons New York 1 81 59
11. For recent reviews, see: H.M.L. Davies, and J. Nikolai Org. Biomol. Chem. 3 2005 4176 4187
12. G.S. Singh Curr. Org. Synth. 2 2005 377 391
13. M.M. Diaz-Requejo, and P.J. Pérez J. Organomet. Chem. 690 2005 5441 5450
14. A.G.H. Wee Curr. Org. Synth. 3 2006 499 555
15. Z. Zhang, and J. Wang Tetrahedron 64 2008 6577 6605
16. C.N. Slattery, A. Ford, and A.R. Maguire Tetrahedron 66 2010 6681 6705
17. M.P. Doyle, R. Duffy, M. Ratnikov, and L. Zhou Chem. Rev. 110 2010 704 724
18. F.C. da Silva, A.K. Jordão, D.R. da Rocha, S.B. Ferreira, A.C. Cunha, and V.F. Ferreira Curr. Org. Chem. 16 2012 224 251
19. Q. Xiang, Y. Zhang, and J. Wang Acc. Chem. Res. 46 2013 236 247
20. G. Masson, S. Py, and Y. Vallée Angew. Chem., Int. Ed. 41 2002 1772 1775
21. G. Masson, P. Cividino, S. Py, and Y. Vallée Angew. Chem., Int. Ed. 42 2003 2265 2268
22. S. Desvergnes, S. Py, and Y. Vallée J. Org. Chem. 70 2005 1459 1462
23. G. Masson, C. Philouze, and S. Py Org. Biomol. Chem. 3 2005 2067 2069
24. C. Pillard, V. Desvergnes, and S. Py Tetrahedron Lett. 48 2007 6209 6213
25. O.N. Burchak, C. Philouze, P.Y. Chavant, and S. Py Org. Lett. 10 2008 3021 3023
26. C.-P. Xu, P.-Q. Huang, and S. Py Org. Lett. 14 2012 2034 2037
27. P. Gilles, and S. Py Org. Lett. 14 2012 1042 1045
28. For recent reviews on reactions involving α-diazocarbonyl compounds as nucleophiles, see: Y. Zhao, and J. Wang Synlett 2005 2886 2892
29. Y. Zhang, and J. Wang Chem. Commun. 2009 5350 5361
30. U. Schöllkopf, and H. Frasnelli Angew. Chem., Int. Ed. 9 1970 301 302
31. A. Padwa, Y.S. Kulkarni, and Z. Zhang J. Org. Chem. 55 1990 4144 4153
32. A. Gioiello, F. Venturoni, B. Natalini, and R. Pellicciari J. Org. Chem. 74 2009 3520 3523
33. H.-F. Cui, L. Wang, L.-Li Yang, J. Nie, Y. Zheng, and J.-A. Ma Tetrahedron 67 2011 8470 8476
34. N. Jiang, Z. Qu, and J. Wang Org. Lett. 3 2001 2989 2992
35. N. Jiang, and J. Wang Tetrahedron Lett. 43 2002 1285 1287
36. N. Jiang, and J. Wang Synlett 2002 149 151
37. N. Jiang, Z. Ma, Z. Qu, X. Xing, L. Xie, and J. Wang J. Org. Chem. 68 2003 893 900
38. Y. Zhao, Z. Ma, X. Zhang, Y. Zou, X. Jin, and J. Wang Angew. Chem., Int. Ed. 43 2004 5977 5980
39. C.G. Goodman, D.T. Do, and J.S. Johnson Org. Lett. 15 2013 2446 2449
40. For the preparation of nitrones, see: A. Dondoni, S. Franco, F. Junquera, F. Merchan, P. Merino, and T. Tejero Synth. Commun. 24 1994 2537 2550
41. P. Deshong, C.M. Dicken, J.M. Leginus, and R.R. Whittle J. Am. Chem. Soc. 106 1984 5598 5602
42. D.D. Dhavale, V.N. Desai, M.D. Sindkhedkar, R.S. Mali, C. Castellari, and C. Trombini Tetrahedron: Asymmetry 8 1997 1475 1486
43. For the addition of organolithium compounds to nitrone 20, see: A. Dondoni, F. Junquera, F.L. Merchan, P. Merino, and T. Tejero Synthesis 1994 1450 1456
44. A. Dondoni, S. Franco, F. Junquera, F.L. Merchan, P. Merino, T. Tejero, and V. Bertolasi Chem. Eur. J. 1 1995 505 520
45. P. Merino, S. Franco, F.L. Merchan, and T. Tejero Tetrahedron: Asymmetry 8 1997 3489 3496
46. P. Merino, E. Castillo, S. Franco, F.L. Merchan, and T. Tejero Tetrahedron: Asymmetry 9 1998 1759 1769
47. P. Merino, S. Franco, N. Garces, F.L. Merchan, and T. Tejero Chem. Commun. 1998 493 494
48. W. Schade, and H.-U. Reissig Synlett 1999 632 634
49. C. Dagoneau, A. Tomassini, J.-N. Denis, and Y. Vallée Synthesis 2001 150 154
50. M. Helms, W. Schade, R. Pulz, T. Watanabe, A. Al-Harrasi, L. Fisera, I. Hlobilová, G. Zahn, and H.-U. Reissig Eur. J. Org. Chem. 2005 1003 1019
51. F. Pfrengle, D. Lentz, and H.-U. Reissig Org. Lett. 11 2009 5534 5537
52. F. Pfrengle, D. Lentz, and H.-U.Beilstein. Reissig J. Org. Chem. 6 2010 75
53. F. Pfrengle, D. Lentz, and H.-U. Reissig Chem. Eur. J. 16 2010 11915 11925
54. P. Merino, S. Anoro, S. Franco, J.M. Gascon, V. Martin, F.L. Merchan, J. Revuelta, T. Tejero, and V. Tunon Synth. Commun. 30 2000 2989 3021
55. N.S. Karanjule, S.D. Markad, V.S. Shinde, and D.D.J. Dhavale Org. Chem. 71 2006 4667 4670
56. For the addition of organolithium compounds to nitrone 21, see: A. Dondoni, S. Franco, F. Junquera, F.L. Merchan, P. Merino, T. Tejero, and V. Bertolasi Chem. Eur. J. 1 1995 505 520
57. A. Dondoni, F. Junquera, F.L. Merchan, P. Merino, M.-C. Scherrmann, and T. Tejero J. Org. Chem. 62 1997 5484 5496
58. E.-L. Tsou, Y.-T. Yeh, P.-H. Liang, and W.-C. Cheng Tetrahedron 65 2009 93 100
59. W.-B. Wang, M.-H. Huang, Y.-X. Li, P.-X. Rui, X.-G. Hu, W. Zhang, J.-K. Su, Z.-L. Zhang, J.-S. Zhu, W.-H. Xu, X.-Q. Xie, Y.-M. Jia, and C.-Y. Yu Synlett 2010 488 492 For the synthesis of sugar-derived cyclic nitrones, see
60. Y.-F. Chang, C.-W. Guo, T.-H. Chan, Y.-W. Pan, E.-L. Tsou, and W.-C. Cheng Mol. Divers. 15 2011 203 214
61. F. Cardona, E. Faggi, F. Liguori, M. Cacciarini, and A. Goti Tetrahedron Lett. 44 2003 2315 2318
62. A.T. Carmona, R.H. Wightman, I. Robina, and P. Vogel Helv. Chim. Acta 86 2003 3066 3073
63. For the addition of organolithium reagents to nitrone 24, see: P. Merino, J. Revuelta, T. Tejero, S. Cicchi, and A. Goti Eur. J. Org. Chem. 2004 776 782
64. P. Merino, I. Delso, T. Tejero, F. Cardona, M. Marradi, E. Faggi, C. Parmeggiani, and A. Goti Eur. J. Org. Chem. 2008 2929 2947
65. V. Liautard, A.E. Christina, V. Desvergnes, and O.R. Martin J. Org. Chem. 71 2006 7337 7345
66. For the addition of organometallic compounds to nitrone 25, see: C. Liu, H. Kang, R.H. Wightman, and S. Jiang Tetrahedron Lett. 54 2013 1192 1194 See also reference 4e
67. O. Tamura, A. Toyao, and H. Ishibashi Synlett 2002 1344 1346
68. For the addition of organometallic compounds to nitrone 26, see: K.P. Kaliappan, P. Das, S.T. Chavan, and S.G. Sabharwal J. Org. Chem. 74 2009 6266 6274
69. Y. Fu, Y. Liu, Y. Chen, H.M. Huegel, M. Wang, D. Huang, and Y. Hu Org. Biomol. Chem. 10 2012 7669 7672