Diastereoselective access to trans -2-substituted cyclopentylamines

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5128-5131

  Joosten, Antoine ^a   Lambert, Émilie ^a   Vasse, Jean Luc ^a   Szymoniak, Jan ^a  

^a UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANILIDE; CYCLOPENTANE 1,2 DIAMINE; CYCLOPENTANE DERIVATIVE; CYCLOPENTANE-1,2-DIAMINE; LEWIS ACID; OXAZOLE DERIVATIVE; OXAZOLIDINE; RODOCAINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMINES; ANILIDES; CYCLIZATION; CYCLOPENTANES; LEWIS ACIDS; MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM;

EID: 78449295221     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102038x     Document Type: Article

References (42)

1. Gademann, K.; Hinterman, T.; Schreiber, J. V. Curr. Med. Chem. 1999, 6, 905-925
2. Juaristi, E.; Lopez-Ruiz, H. Curr. Med. Chem. 1999, 6, 983-1004
3. Scarborough, R. M. Curr. Med. Chem. 1999, 6, 971
4. Fulop, F. Chem. Rev. 2001, 101, 2181-2204
5. Iwamoto, T.; Tsujii, E.; Ezaki, M.; Fujie, A.; Hashimoto, S.; Okuhara, M.; Kohsaka, M.; Imanaka, H.; Inamoto, Y.; Sakane, K. J. Antibiotics 1990, 43, 1-7
6. Kawabata, K.; Inamoto, Y.; Sakane, K.; Iwamoto, T.; Hashimoto, S. J. Antibiot. 1990, 43, 513-518
7. Myers, M. C.; Witschi, M. A.; Lariona, N. V.; Franck, J. M.; Haynes, R. D.; Hara, T.; Grajkowski, A.; Appella, D. H. Org. Lett. 2003, 5, 2695-2698
8. Pokorski, J. K.; Witschi, M. A.; Purnell, B. L.; Appella, D. H. J. Am. Chem. Soc. 2004, 126, 15067-15073
9. Zhang, N.; Appella, D. H. J. Am. Chem. Soc. 2007, 129, 8424-8425
10. Larrow, J. F.; Jacobsen, E. N. Top. Organomet. Chem. 2004, 6, 123-152
11. Dominguez, B.; Hodnett, N. S.; Lloyd-Jones, G. C. Angew. Chem., Int. Ed. 2001, 40, 4289-4291
12. Daly, A. M.; Gilheavy, D. G. Tetrahedron: Asymmetry 2003, 14, 127-137
13. For asymmetric synthesis of cispentacin, see
14. Aggarwal, V. K.; Roseblade, S. J.; Barrell, J. K.; Alexander, R. Org. Lett. 2002, 4, 1227-1229
15. Aggarwal, V. K.; Roseblade, S.; Alexander, R. Org. Biomol. Chem. 2003, 1, 684-691 For asymmetric synthesis of trans -pentacin, see: Chippendale, A. M.; Davies, S. G.; Iwamoto, K.; Parkin, R. M.; Smethurst, C. A. P.; Smith, A. D.; Rodriguez-Solla, H. Tetrahedron 2003, 59, 3253-3265
16. For the preparation of trans -diaminocyclopentane by resolution, see: González-Sabín, J.; Gotor, V.; Rebolledo, F. J. Org. Chem. 2007, 72, 1309-1314
17. Pena, C.; González-Sabín, J.; Rebolledo, F.; Gotor, V. Tetrahedron: Asymmetry 2008, 19, 751-755
18. Xu, Q.; Appella, D. H. J. Org. Chem. 2006, 71, 8655-8657
19. Schneider, C. Angew. Chem., Int. Ed. 2009, 48, 2-5
20. Page, M. F. Z.; Jalisatgi, S. S.; Maderna, A.; Hawthorne, M. F. Synthesis 2008, 555-563
21. Blyumin, E. V.; Gallon, H. J.; Yudin, A. K. Org. Lett. 2007, 9, 4677-4680
22. Fujimori, I.; Mita, T.; Maki, K.; Shiro, M.; Sato, A.; Furusho, S.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 16438-16439
23. Minakata, S.; Okada, Y.; Oderaotoshi, Y.; Komatsu, M. Org. Lett. 2005, 7, 3509-3512
24. Vasse, J.-L.; Joosten, A.; Denhez, C.; Szymoniak, J. Org. Lett. 2005, 7, 4887-4889
25. Godineau, E.; Schenk, K.; Landais, Y. J. Org. Chem. 2008, 73, 6983-6993
26. Miyata, O.; Muroya, K.; Kobayashi, T.; Yamanaka, R.; Kajisa, S.; Koide, J.; Naito, T. Tetrahedron 2002, 58, 4459-4479
27. Bartell, P. A.; McLaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 110, 1633-1634
28. The trans relative configuration in 1a was deduced from NOESY experiment.
29. Tang, W.; Wu, S.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 9570-9571
30. Gardiner, J.; Anderson, K. H.; Downard, A.; Abell, A. D. J. Org. Chem. 2004, 69, 3375-3382
31. Henshall, T.; Parnell, E. W. J. Chem. Soc 1962, 661
32. Hermans, H.; Hubert, K. F.; Knaeps, G. A.; Willems, J. J. M. U.S. Patent No. 3,679,686, 1972.
33. 6 was prepared in 83% yield from the corresponding acyl chloride and aniline derivative according to
34. Tenthorey, P. A.; DiRubio, R. L.; Feldman, H. S.; Takman, B. H. J. Med. Chem. 1979, 22, 1182-1186
35. Rishel, M. J.; Hecht, S. M. Org. Lett. 2001, 3, 2867-2869
36. The enantiomeric excess was confirmed by chiral HPLC after derivatization. See ref 6a.
37. 2 was added at -10°C, and addition at higher temperature increases the racemization.
38. For the synthesis of optically pure 2-substituted pent-4-enal derivatives via the diastereoselective allylation of pseudoephedrine-derived amides followed by reduction, see
39. Myers, A. G.; Yang, B. H.; Chen, H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361-9362
40. Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1995, 117, 8488-8489
41. Myers, A. G.; Gleason, J. L.; Yoon, T.; Kung, D. W. J. Am. Chem. Soc. 1997, 119, 656-673
42. Myers, A. G.; Schnider, P.; Yoon, T.; Kung, D. W. J. Org. Chem. 1999, 64, 3322-3327