The [2+2] photocycloaddition of uracil derivatives with ethylene as a general route to cis-cyclobutane β-amino acids

Synlett

Volumn , Issue 9, 2006, Pages 1394-1398

  Gauzy, Christine ^a   Saby, Bertrand ^a   Pereira, Elisabeth ^a   Faure, Sophie ^a   Aitken, David J ^a  

^a Université Blaise Pascal   (France)

Author keywords

amino acids; 2+2 photocycloaddition; Cyclobutane; Substituent effects; Uracils

Indexed keywords

2 AMINOCYCLOBUTANE 1 CARBOXYLIC ACID; BETA AMINO ACID; CYCLOBUTANE DERIVATIVE; ETHYLENE; FUSED HETEROCYCLIC RINGS; SINGLE HETEROCYCLIC RINGS; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DEGRADATION; HYDROLYSIS; PHOTOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33745393067     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-941571     Document Type: Article

References (53)

1. (a) Seebach, D.; Matthews, J. L. Chem. Commun. 1997, 2015.
2. (b) Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
3. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powel, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1996, 118, 13071.
4. (a) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
5. (b) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1.
6. (c) Steer, D. L.; Lew, R. A.; Perlmutter, P.; Smith, A. I.; Aguilar, M.-I. Curr. Med. Chem. 2002, 9, 811.
7. (d) Seebach, D.; Beck, A. K.; Bierbaume, D. J. Chem. Biodiversity 2004, 1, 1111.
8. For leading references, see: (a) Fülöp, F. Chem. Rev. 2001, 101, 2181.
9. (b) North, M. J. Peptide Sci. 2000, 6, 301.
10. (c) Kuhl, A.; Hahn, M. G.; Dumić, M.; Mittendorf, J. Amino Acids 2005, 29, 89.
11. (d) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
12. (a) Izquierdo, S.; Rùa, F.; Sbai, A.; Parella, T.; Alvarez-Larena, A.; Branchadell, V.; Ortuño, R. M. J. Org. Chem. 2005, 70, 7963.
13. (b) Izquierdo, S.; Martín-Vilà, M.; Moglioni, A. G.; Branchadell, V.; Ortuño, R. M. Tetrahedron: Asymmetry 2002, 13, 2403.
14. (c) Martín-Vilà, M.; Muray, E.; Aguado, G. P.; Alvarez-Larena, A.; Branchadell, V.; Minguillón, C.; Giralt, E.; Ortuño, R. M. Tetrahedron: Asymmetry 2000, 11, 3569.
15. Different synthetic approaches have been outlined: (a) Ortuno, R. M.; Moglioni, A. G.; Moltrasio, G. Y. Curr. Org. Chem. 2005, 9, 237.
16. (b) Bolm, C.; Schiffers, I.; Atodiresei, I.; Hackenberger, C. P. R. Tetrahedron: Asymmetry 2003, 14, 3455.
17. (c) Kennewell, P. D.; Matharu, S. S.; Taylor, J. B.; Westwood, R.; Sammes, P. G. J. Chem. Soc., Perkin. Trans. 1 1982, 2563.
18. (d) Brannock, K. C.; Bell, A.; Burpitt, R. D.; Kelly, C. A. J. Org. Chem. 1964, 29, 801.
19. (a) Mittendorf, J.; Kunisch, F.; Matzke, M.; Militzer, H.-C.; Schmidt, A.; Schönfeld, W. Bioorg. Med. Chem. Lett. 2003, 13, 433.
20. (b) Mitsudo, T.-A.; Zhang, S.-W.; Satake, N.; Kondo, T.; Watanabe, Y. Tetrahedron Lett. 1992, 33, 5533.
21. (c) Stoermer, R.; Schenk, F. Chem. Ber. 1928, 61, 2318.
22. Yuan, P.; Driscoll, M. R.; Raymond, S. J.; Hansen, D. E.; Blatchly, R. A. Tetrahedron Lett. 1994, 35, 6195.
23. Recently, an elegant intramolecular [2+2]-photocycloaddition approach was described for the preparation of constrained bicyclic β-amino acid derivatives: Basler, B.; Schuster, O.; Bach, T. J. Org. Chem. 2005, 70, 9798.
24. Aitken, D. J.; Gauzy, C.; Pereira, E. Tetrahedron Lett. 2002, 43, 6177.
25. Ethylene is a convenient partner for intermolecular [2+2] photocycloadditions with enone-type reagents; for illustrative recent examples, see: (a) Gu, X.; Xian, M.; Roy-Faure, S.; Bolte, J.; Aitken, D. J.; Gefflaut, T. Tetrahedron Lett. 2006, 47, 193.
26. (b) Furutani, A.; Katayama, K.; Uesima, Y.; Ogura, M.; Tobe, Y.; Kurosawa, H.; Tsutsumi, K.; Morimoto, T.; Kakiuchi, K. Chirality 2006, 18, 217.
27. (c) Gauzy, C.; Pereira, E.; Faure, S.; Aitken, D. J. Tetrahedron Lett. 2004, 45, 7095.
28. (d) Piers, E.; Orellana, A. Synthesis 2001, 2138.
29. (e) de March, P.; Figueredo, M.; Font, J.; Raya, J. Org. Lett. 2000, 2, 163.
30. (f) Tsujishima, H.; Nakatani, K.; Shimamoto, K.; Shigeri, Y.; Yumoto, N.; Ohfune, Y. Tetrahedron Lett. 1998, 39, 1193.
31. (a) Wagner, P. J.; Bucheck, D. J. J. Am. Chem. Soc. 1970, 92, 181.
32. (b) Khattak, M. N.; Wang, S. Y. Tetrahedron 1972, 28, 945.
33. (c) Birnbaum, G. I.; Dunston, J. M.; Szabo, A. G. Tetrahedron Lett. 1971, 12, 947.
34. (d) Shim, S. C.; Lee, S. H. Photochem. Photobiol. 1979, 29, 1035.
35. (a) Wexler, A. J.; Balchunis, R. J.; Swenton, J. S. J. Org. Chem. 1984, 49, 2733.
36. (b) Wexler, A. J.; Hyatt, J. A.; Raynolds, P. W.; Cottrell, C.; Swenton, J. S. J. Am. Chem. Soc. 1978, 100, 512.
37. (c) Wexler, A. J.; Swenton, J. S. J. Am. Chem. Soc. 1976, 98, 1602.
38. (a) Li, S. S.; Sun, X. L.; Ogura, H.; Konda, Y.; Sasaki, T.; Toda, Y.; Takayanagi, H.; Harigaya, Y. Chem. Pharm. Bull. 1995, 43, 144.
39. (b) Ishikawa, I.; Itoh, T.; Takayanagi, H.; Oshima, J.-i.; Kawahara, N.; Mizuno, Y.; Ogura, H. Chem. Pharm. Bull. 1991, 39, 1922.
40. Maleski, R.; Morrison, H. Mol. Photochem. 1972, 4, 507.
41. Aoyama, H.; Hatori, H. Tetrahedron 1990, 46, 3781.
42. Compound 1c was obtained from 5-iodouracil by Suzuki reaction with phenylboronic acid.
43. Fang, W.-P.; Cheng, Y.-T.; Cheng, Y.-R.; Cherng, Y.-J. Tetrahedron 2005, 61, 3107.
44. Harnden, M. R.; Hurst, D. T. Aust. J. Chem. 1990, 43, 47.
45. Goto, S.; Yamanaka, A.; Kagara, K.; Yazawa, H. Chem. Express 1988, 3, 211.
46. Compound 1r was obtained by esterification of orotic acid in excess n-hexanol (as solvent) in the presence of anhydrous HCl.
47. Kunieda, T.; Witkop, B. J. Am. Chem. Soc. 1971, 93, 3493.
48. (a) Ingold, C. K.; Sako, S.; Thorpe, J. F. J. Chem. Soc. Trans. 1922, 121, 1177.
49. (b) Garcia, M. J.; Azerad, R. Tetrahedron: Asymmetry 1997, 8, 85.
50. Rachina, V.; Blagoeva, I. Synthesis 1982, 967.
51. 13C NMR data with the literature. See: (a) For 5-oxohexanoic acid (6m): Griesbaum, K.; Miclaus, V.; Jung, I. C.; Quinkert, R.-O. Eur. J. Org. Chem. 1998, 627.
52. (b) For 5-oxo-5-phenylpentanoic acid (6n): Hon, Y.-S.; Lin, S.-W.; Lu, L.; Chen, Y.-J. Tetrahedron 1995, 51, 5019.
53. Aitken, D. J.; Gauzy, C.; Pereira, E. Tetrahedron Lett. 2004, 45, 2359.