Diastereoselective preparation of azetidines and pyrrolidines

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5044-5047

  Feula, Antonio ^a   Male, Louise ^a   Fossey, John S ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AZETIDINES; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PYRROLIDINES; STEREOISOMERISM;

EID: 78049488246     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102215e     Document Type: Article

References (51)

1. Tidwell, T. T. Angew. Chem., Int. Ed. 2008, 47, 1016
2. Berlin, J. M.; Fu, G. C. Angew. Chem., Int. Ed. 2008, 47, 7048
3. Starmans, W. A. J.; Walgers, R. W. A.; Thijs, L.; de Gelder, R.; Smits, J. M. M.; Zwanenburg, B. Tetrahedron 1998, 54, 4991
4. Keller, L.; Sanchez, M. V.; Prim, D.; Couty, F.; Evano, G.; Marrot, J. J. Organomet. Chem. 2005, 690, 2306
5. Lee, Y. H.; Harrowfield, J.; Kim, Y.; Lim, W. T.; Park, Y. C.; Thuery, P. Dalton Trans. 2009, 434
6. Lee, Y. H.; Harrowfield, J. M.; Kim, J. S.; Kim, Y.; Lee, M. H.; Lim, W. T.; Park, Y. C.; Thuery, P. Dalton Trans. 2009, 443
7. Lee, Y. H.; Kim, H. H.; Thuery, P.; Harrowfield, J. M.; Lim, W. T.; Kim, B. J.; Kim, Y. J. Inclusion Phenom. Macrocyclic Chem. 2009, 65, 65
8. Wilken, J.; Erny, S.; Wassmann, S.; Martens, J. Tetrahedron: Asymmetry 2000, 11, 2143
9. Baeg, J. O.; Bensimon, C.; Alper, H. J. Org. Chem. 1995, 60, 253
10. Singh, S.; Crossley, G.; Ghosal, S.; Lefievre, Y.; Pennington, M. W. Tetrahedron Lett. 2005, 46, 1419
11. Yoda, H.; Uemura, T.; Takabe, K. Tetrahedron Lett. 2003, 44, 977
12. Frigola, J.; Pares, J.; Corbera, J.; Vano, D.; Merce, R.; Torrens, A.; Mas, J.; Valenti, E. J. Med. Chem. 1993, 36, 801
13. Schmitt, J. D.; Sharples, C. G.; Caldwell, W. S. J. Med. Chem. 1999, 42, 3066
14. Wang, D. X.; Booth, H.; Lerner-Marmarosh, N.; Osdene, T. S.; Abood, L. G. Drug Dev. Res. 1998, 45, 10
15. Brandi, A.; Cicchi, S.; Cordero, F. M. Chem. Rev. 2008, 108, 3988
16. Robin, S.; Rousseau, G. Eur. J. Org. Chem. 2002, 2002, 3099
17. Hillier, M. C.; Chen, C. Y. J. Org. Chem. 2006, 71, 7885
18. Burkhard, J.; Carreira, E. M. Org. Lett. 2008, 10, 3525
19. Sato, M.; Gunji, Y.; Ikeno, T.; Yamada, T. Synthesis 2004, 1434
20. Secor, H. V.; Edwards, W. B. J. Org. Chem. 1979, 44, 3136
21. de Figueiredo, R. M.; Frohlich, R.; Christmann, M. J. Org. Chem. 2006, 71, 4147
22. Albrecht, Ł.; Jiang, H.; Dickmeiss, G.; Gschwend, B.; Hansen, S. G.; Jørgensen, K. A. J. Am. Chem. Soc. 2010, 132, 9188
23. Varlamov, A. V.; Sidorenko, N. V.; Zubkov, F. I.; Chernishev, A. I.; Turchin, K. F. Khim. Geterotsikl. Soedin. 2004, 1261
24. Varlamov, A. V.; Sidorenko, N. V.; Zubkov, F. I.; Chernyshev, A. I.; Turchin, K. F. Chem. Heterocycl. Compd. (N.Y., NY, U.S.) 2004, 40, 1097
25. Berthe, B.; Outurquin, F.; Paulmier, C. Tetrahedron Lett. 1997, 38, 1393
26. Outurquin, F.; Pannecoucke, X.; Berthe, B.; Paulmier, C. Eur. J. Org. Chem. 2002, 1007
27. Pannecoucke, X.; Outurquin, F.; Paulmier, C. Eur. J. Org. Chem. 2002, 995
28. Corey, E. J.; Loh, T. P.; Achyutharao, S.; Daley, D. C.; Sarshar, S. J. Org. Chem. 1993, 58, 5600
29. Robin, S.; Rousseau, G. Eur. J. Org. Chem. 2000, 3007
30. For a review of 5-endo electrophile assisted ring closures see ref 17.
31. Knight, D. W. In Progress in Heterocyclic Chemistry; Gordon, W. G.; Thomas, L. G., Eds.; Elsevier: Amsterdam, The Netherlands, 2002; Vol. 14, p 19.
32. Knight, D. W.; Redfern, A. L.; Gilmore, J. Tetrahedron Lett. 1998, 39, 8909
33. Ichikawa, J.; Lapointe, G.; Iwai, Y. Chem. Commun. 2007, 2698
34. Lee, W. S.; Jang, K. C.; Kim, J. H.; Park, K. H. Chem. Commun. 1999, 251
35. Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2003, 44, 5209
36. Drouillat, B.; Couty, F.; David, O.; Evano, G.; Marrot, J. Synlett 2008, 2008, 1345
37. Durrat, F.; Sanchez, M. V.; Couty, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2008, 3286
38. Couty, F.; Kletskii, M. THEOCHEM 2009, 908, 26
39. Keck, G. E.; Enholm, E. J. J. Org. Chem. 1985, 50, 146
40. Davies, S. G.; Nicholson, R. L.; Price, P. D.; Roberts, P. M.; Russell, A. J.; Savory, E. D.; Smith, A. D.; Thomson, J. E. Tetrahedron: Asymmetry 2009, 20, 758
41. For proton NMR spectra comparing post work-up and post column chromatography on obtained 2d see the Supporting Information.
42. Pyridinium iodide formation was postulated. Cf.
43. Chen, W.; Elfeky, S. A.; Nonne, Y.; Male, L.; Ahmed, K.; Amiable, C.; Axe, P.; Yamada, S.; James, T. D.; Bull, S. D.; Fossey, J. S. Chem. Commun. DOI: 10.1039/c0cc01420f. Published Online: July 5, 2010.
44. Richter, I.; Minari, J.; Axe, P.; Lowe, J. P.; James, T. D.; Sakurai, K.; Bull, S. D.; Fossey, J. S. Chem. Commun. 2008, 1082
45. The X-ray crystal structure of 2b consists of two crystallographically independent molecules, the geometry of which are very similar to one another and of which only one has been shown.
46. Vagg, R.; Chapman, S. Addiction 2005, 100, 701
47. Denton, T. T.; Zhang, X. D.; Cashman, J. R. J. Med. Chem. 2005, 48, 224
48. Barlow, R. B.; Hamilton, J. T. Br. J. Pharmacol. Chemother. 1962, 18, 510
49. Pogocki, D.; Ruman, T.; Danilczuk, M.; Danilczuk, M.; Celuch, M.; Walajtys-Rode, E. Eur. J. Pharmacol. 2007, 563, 18
50. The trans: cis ratio for 6 was 1:1 when the benzylamine addition step was carried out in DMF (71% yield).
51. Scrafton, D. K.; Taylor, J. E.; Mahon, M. F.; Fossey, J. S.; James, T. D. J. Org. Chem. 2008, 73, 2871