Highly selective indium mediated allylation of unprotected pentosylamines

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1536-1539

  Behr, Jean Bernard ^a   Hottin, Audrey ^a   Ndoye, Alpha ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84858635517     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol3002656     Document Type: Article

References (46)

1. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831-1833
2. Yadav, J. S.; Antony, A.; George, J.; Reddy, B. V. S. Eur. J. Org. Chem. 2010, 591-605
3. Augé, J.; Lubin-Germain, N.; Uziel, J. Synthesis 2007, 1739-1764
4. Yamaguchi, Y.; Hashimoto, M.; Tohyama, K.; Kimura, M. Tetrahedron Lett. 2011, 52, 913-915
5. Sugiura, M.; Hirano, K.; Kobayashi, S. Org. Synth. 2006, 83, 170
6. Lievens, S. C.; Molinski, T. J. Am. Chem. Soc. 2006, 128, 11764-11765
7. Hansen, F. G.; Bundgaard, E.; Madsen, R. J. Org. Chem. 2005, 70, 10139-10142
8. Palmelund, A.; Madsen, R. J. Org. Chem. 2005, 70, 8248-8251
9. Choi, S.-K.; Lee, S.; Whitesides, G. M. J. Org. Chem. 1996, 61, 8739-8745
10. Gao, J.; Haerter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714-3715
11. Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500-5507
12. Beuchet, P.; Le Marrec, N.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959-5960
13. Svengas, R. G.; Segade, Y.; Jimenez, C.; Rodriguez, J. Tetrahedron 2011, 67, 2617-2622
14. Kim, S. J.; Jang, D. O. J. Am. Chem. Soc. 2010, 132, 12168-12169
15. Kouznetsov, V. V.; Mendez, L. Y. V. Synthesis 2008, 491-506
16. Law, M. C.; Cheung, T. W.; Wong, K.-Y.; Chan, T. H. J. Org. Chem. 2007, 72, 923-929
17. Vilaivan, T.; Winotapan, C.; Banphavichit, V.; Shinada, T.; Ohfune, Y. J. Org. Chem. 2005, 70, 3464-3471
18. Ding, H.; Friestad, G. K. Synthesis 2005, 2815-2829
19. Yanada, R.; Kaieda, A.; Takemoto, Y. J. Org. Chem. 2001, 66, 7516-7518
20. Isbell, H. S.; Frush, H. L. J. Org. Chem. 1958, 23, 1309-1319
21. Rajender, A.; Rao, J.-P.; Rao, B. V. Tetrahedron: Asymmetry 2011, 22, 1306-1311
22. Behr, J.-B.; Gainvors-Claisse, A.; Belarbi, A. Nat. Prod. Res. A 2006, 20, 1308-1314
23. Djebaili, M.; Behr, J.-B. J. Enz. Inihib. Med. Chem. 2005, 20, 123-127
24. Schönemann, W.; Gallienne, E.; Compain, P.; Ikeda, K.; Asano, N.; Martin, O. R. Bioorg. Med. Chem. 2010, 18, 2645-2650
25. Behr, J.-B.; Erard, A.; Guillerm, G. Eur. J. Org. Chem. 2002, 1256-1262
26. Behr, J.-B.; Guillerm, G. Tetrahedron: Asymmetry 2002, 13, 111-113
27. Schweizer, F. Angew. Chem., Int. Ed. 2002, 41, 230-253
28. Cipolla, L.; La Ferla, B.; Peri, F.; Nicotra, F. Chem. Commun. 2000, 1289-1290
29. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677-1716
30. Liautard, V.; Desvergnes, V.; Itoh, K.; Liu, H.-w.; Martin, O. R. J. Org. Chem. 2008, 73, 3103-3115
31. Decroocq, C.; Laparra, L. M.; Rodriguez-Lucena, D.; Compain, P. J. Carb. Chem 2011, 30, 559-574
32. Capello, C.; Fischer, U.; Hungerbühler, K. Green Chem. 2007, 9, 927-934
33. Dangerfield, E. M.; Plunkett, C. H.; Win-Mason, A. L.; Stocker, B. L.; Timmer, M. S. M. J. Org. Chem. 2010, 75, 5470-5477
34. Dangerfield, E. M.; Timmer, M. S. M.; Stocker, B. L. Org. Lett. 2009, 11, 535-538
35. Zhu, Y.; Pan, Q.; Thibaudeau, C.; Zhao, S.; Carmichael, I.; Serianni, A. S. J. Org. Chem. 2006, 71, 466-479
36. Chavis, C.; De Gourcy, C.; Dumont, F.; Imbach, J.-L. Carbohydr. Res. 1983, 113, 1-20
37. Direct evaporation of the volatiles afforded a white precipitate with unanalyzable broad NMR signals. Alternatively, when aqueous ammonia was added both to neutralize the acidic reaction mixture and to precipitate indium hydroxyde, evaporation of the liquor yielded only trace amount of material, most of the organic fraction being incorporated into the insoluble solid. In(III) forms stable complexes with N -containing ligands: Mahmoud, S. A.; Issa, I. M.; El-Gyar, S. A. Monatsh. Chem. 1980, 111, 431-438
38. Bowyer, W. J.; Singaram, B.; Sessler, A. M. Tetrahedron 2011, 67, 7449-7460
39. Koszinowski, K. J. Am. Chem. Soc. 2010, 132, 6032-6040
40. Haddad, T. D.; Hirayama, L. C.; Singaram, B. J. Org. Chem. 2010, 75, 642-649
41. Behr, J.-B.; Kalla, A.; Harakat, D.; Plantier-Royon, R. J. Org. Chem. 2008, 73, 3612-3615
42. Desvergnes, S.; Vallée, Y.; Py, S. Org. Lett. 2008, 10, 2967-2970
43. Veith, U.; Jäger, V. Chem. Commun. 1996, 329-330
44. Toyooka, N. In Asymmetric Synthesis of Nitrogen Heterocycles; Royer, J. Ed.; Wiley: Weinheim, 2009; pp 98-107.
45. Woodward, C. P.; Spiccia, N. D.; Jackson, W. R.; Robinson, A. J. Chem. Commun. 2011, 47, 779-781
46. Compain, P. Adv. Synth. Catal. 2007, 349, 1829-1846