Synthesis of novel and uniquely shaped 3-azabicyclo[4.2.0]octan-4-one derivatives by sequential Ugi/[2+2] ene-enone photocycloadditions

Organic Letters

Volumn 9, Issue 7, 2007, Pages 1299-1302

  Akritopoulou Zanze, Irini ^a   Whitehead, Alan ^a   Waters, Jan E ^a   Henry, Rodger F ^a   Djuric, Stevan W ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34147145356     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070164l     Document Type: Article

References (25)

1. For reviews, see: (a) Dömling, A. Chem. Rev. 2006, 106, 17-89.
2. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
3. (c) Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51-80.
4. (d) Zhu, J. Eur. J. Org. Chem. 2003, 1133-1144.
5. For early examples of post-Ugi modifications, see: (a) Tempest, P.; Ma, V.; Kelly, M. G.; Jones, W.; Hulme, C. Tetrahedron Lett. 2001, 42, 4963-4968.
6. (b) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851-1854.
7. (c) Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227-7230.
8. (d) Hulme, C.; Morrissette, M. M.; Volz, F. A.; Burns, C. J. Tetrahedron Lett. 1998, 39, 1113-1116.
9. (e) Park, S. J.; Keum, G.; Kang, S. B.; Koh, H. Y.; Kim, Y. Tetrahedron Lett. 1998, 39, 7109-7112.
10. (f) Strocker, A. M.; Keating, T. A.; Tempest, P. A.; Armstrong, R. W. Tetrahedron Lett. 1996, 37, 1149-1152.
11. (g) Short, K. M.; Ching, B. W.; Mjalli, A. M. M. Tetrahedron Lett. 1996, 37, 7489-7492.
12. Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 417-420.
13. Akritopoulou-Zanze, I.; Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 3421-3423.
14. Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 8439-8441.
15. (a) Crimmins, M. T. Chem. Rev. 1988, 88, 1453-1473.
16. (b) Fleming, S. A.; Bradford, C. L.; Gao, J. J. Mol. Supramol. Photochem. 1997, 1, 187-243.
17. Griesbeck, A. G.; Fiege, M. Mol. Supramol. Photochem. 2000, 6, 33-100.
18. The reaction was performed in a capped vial, sparged with argon, and placed in 3-inch proximity to a medium pressure, 450 W, mercury lamp. When the reaction was performed in an immersion well reactor equipped with a quartz Pen-Ray 5.5 W, low-pressure, cold cathode, mercury lamp (Penn, J. H.; Orr, R. D. J. Chem. Educ. 1989, 66, 86-88.), the reaction was complete in 2 h. However, we preferred the former method due to the convenience of using vials as well as the ability to perform multiple reactions concurrently.
19. Haywood, D. J.; Reid, S. T. Tetrahedron Lett. 1979, 20, 2637-2638.
20. Brandes, S.; Selig, P.; Bach, T. Syn. Lett. 2004, 14, 2588-2590.
21. For a detailed description of stereochemical assignments and justification, see Supporting Information.
22. 2O and deprotection with aq LiOH in THF according to: Fonteneau, L; Rosa, S.; Buisson, D. Tetrahedron: Assymetry 2002, 13, 579-585.
23. (a) Le blanc, S.; Pete, J. P.; Piva, O. Tetrahedron Lett. 1993, 34, 635-638.
24. (b) Faure, S.; Piva-Le Blanc, S.; Piva, O. Tetrahedron Lett. 1999, 40, 6001-6004.
25. See Supporting Information.