Synthesis of substituted cyclohexenyl-based β-amino acids by ring-closing metathesis

Organic Letters

Volumn 4, Issue 21, 2002, Pages 3663-3666

  Abell, Andrew D ^a   Gardiner, James ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CYCLOHEXANE DERIVATIVE; CYCLOHEXENE; CYCLOHEXENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

AMINO ACIDS; CYCLOHEXANES; CYCLOHEXENES; MOLECULAR STRUCTURE;

EID: 0037126284     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0266121     Document Type: Article

References (32)

1. For a recent review in this area, see: Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219.
2. Jenkins, C. L.; Raines, R. T. Nat. Prod. Rep. 2002, 19 (1), 49.
3. Barchi, J. J.; Huang, X.; Appella, D. H.; Christianson, L. A.; Durell, S. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 2711. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206 and references therein. Abele, S.; Guichard, G.; Seebach, D. Helv. Chim. Acta 1998, 81, 2141 and references therein. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
4. Barchi, J. J.; Huang, X.; Appella, D. H.; Christianson, L. A.; Durell, S. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 2711. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206 and references therein. Abele, S.; Guichard, G.; Seebach, D. Helv. Chim. Acta 1998, 81, 2141 and references therein. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
5. Barchi, J. J.; Huang, X.; Appella, D. H.; Christianson, L. A.; Durell, S. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 2711. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206 and references therein. Abele, S.; Guichard, G.; Seebach, D. Helv. Chim. Acta 1998, 81, 2141 and references therein. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
6. Barchi, J. J.; Huang, X.; Appella, D. H.; Christianson, L. A.; Durell, S. R.; Gellman, S. H. J. Am. Chem. Soc. 2000, 122, 2711. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206 and references therein. Abele, S.; Guichard, G.; Seebach, D. Helv. Chim. Acta 1998, 81, 2141 and references therein. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913. Seebach, D.; Overhand, M.; Kühnle, F. N. M.; Martinoni, B.; Oberer, L.; Hommel, U.; Widmer, H. Helv. Chim. Acta 1996, 79, 913.
7. Fülöp, F. Chem. Rev. 2001, 101, 2181.
8. Appella, D. H.; LePlae, P. R.; Raguse, T. L.; Gellman, S. H. J. Org. Chem. 2000, 65, 4766.
9. Appella, D. H.; LePlae, P. R.; Raguse, T. L.; Gellman, S. H. J. Org. Chem. 2000, 65, 4766. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206. Appella, D. H.; Christianson, L. A.; Karle, I. L.; Powell, D. R.; Gellman, S. H. J. Am. Chem. Soc. 1999, 121, 6206. Xu, D.; Prasad, K.; Repi, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445. Enders, D.; Wiedemann, J. Leibigs. Ann./Recl. 1997, 699. Kobayashi, S.; Kamiyama, K.; Ohno, M., J. Org. Chem. 1990, 55, 1169. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230.
10. Schultz, A. G. Acc. Chem. Res. 1990, 23, 207. Enders, D.; Wiedemann, J. Leibigs. Ann./Recl. 1997, 699. Kobayashi, S.; Kamiyama, K.; Ohno, M., J. Org. Chem. 1990, 55, 1169. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230.
11. Schultz, A. G. Acc. Chem. Res. 1990, 23, 207. Xu, D.; Prasad, K.; Repi, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445. Xu, D.; Prasad, K.; Repi, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445. Kobayashi, S.; Kamiyama, K.; Ohno, M., J. Org. Chem. 1990, 55, 1169. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230.
12. Schultz, A. G. Acc. Chem. Res. 1990, 23, 207. Xu, D.; Prasad, K.; Repi, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445. Enders, D.; Wiedemann, J. Leibigs. Ann./Recl. 1997, 699. Enders, D.; Wiedemann, J. Leibigs. Ann./Recl. 1997, 699. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230.
13. Schultz, A. G. Acc. Chem. Res. 1990, 23, 207. Xu, D.; Prasad, K.; Repi, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445. Enders, D.; Wiedemann, J. Leibigs. Ann./Recl. 1997, 699. Kobayashi, S.; Kamiyama, K.; Ohno, M., J. Org. Chem. 1990, 55, 1169. Kobayashi, S.; Kamiyama, K.; Ohno, M., J. Org. Chem. 1990, 55, 1169.
14. Schultz, A. G. Acc. Chem. Res. 1990, 23, 207. Xu, D.; Prasad, K.; Repi, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 1445. Enders, D.; Wiedemann, J. Leibigs. Ann./Recl. 1997, 699. Kobayashi, S.; Kamiyama, K.; Ohno, M., J. Org. Chem. 1990, 55, 1169. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230. Nohira, H.; Ehara, K.; Miyashita, A. Bull. Chem. Soc. Jpn. 1970, 43, 2230. Wipf, P.; Wang, X. Tetrahedron Lett. 2000, 8747.
15. Wipf, P.; Wang, X. Org. Lett. 2002, 4, 1197.
16. Wipf, P.; Wang, X. Org. Lett. 2002, 4, 1197. Wipf, P.; Wang, X. Tetrahedron Lett. 2000, 8747. Wipf, P.; Wang, X. Tetrahedron Lett. 2000, 8747.
17. For a review on the application of ring-closing metathesis to nitrogen-containing heterocycles, alkaloids, and peptidomimetics, see: Phillips, A. J.; Abell, A. D. Aldrichimica Acta 1999, 32, 75.
18. Podlech, J.; Seebach, D. Leibigs Ann. 1995, 1217 and references therein.
19. Seebach, D.; Esterman, H. Tetrahedron Lett. 1987, 28, 3103. Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 20, 971.
20. Seebach, D.; Esterman, H. Tetrahedron Lett. 1987, 28, 3103. Seebach, D.; Esterman, H. Helv. Chim. Acta 1988, 71, 1824. Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 20, 971. Seebach, D.; Esterman, H. Helv. Chim. Acta 1988, 71, 1824.
21. Seebach, D.; Wasmuth, D. Angew. Chem. 1981, 20, 971.
22. Grubbs, R. H.; Miller, S. J.; Blackwell, H. E. J. Am. Chem. Soc. 1996, 118, 9606.
23. Comparable results were obtained using Grubbs second generation catalyst, tricyclohexylphosphine [1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazole-2-ylidene benzylidene]ruthenium(IV) dichloride.
24. Appella, D. H.; LePlae, P. R.; Raguse, T. L.; Gellman, S. H. J. Org. Chem. 2000, 65, 4766.
25. Duan, J.; Ott, G.; Chen, L.; Lu, Z.; Maduskuie, T. P., Jr.; Voss, M. E.; Xue, C.-B. PCT Int. Appl. WO 0170673 A2 20010927, 2001.
26. Evans, D. A.; Wu, L. D.; Wiener, J. J.; Johnson, J. S.; Ripin, D. H. B.; Tedrow J. S. J. Org. Chem. 1999, 64, 6411.
27. Sibi, M. P.; Deshpande, P. K. J. Chem. Soc., Perkin Trans. 1 2000, 1461.
28. Evans, D. A.; Britton, T. C.; Dorow, R. L.; Dellaria, J. F., Jr. Tetrahedron 1998, 44, 5525.
29. 16 -10.09° (c 1.1 MeOH)).
30. int = 0.0221) and used in the full-matrix least-squares refinement. The structure was solved by direct methods. Hydrogen atoms were fixed in idealized positions. All non-hydrogen atoms were refined with anisotropic atomic displacement parameters. Neutral scattering factors and anomalous dispersion corrections for non-hydrogen atoms were taken from Ibers and Hamilton (Ibers, J. A., Hamilton, W. C., Eds.; International Tables for Crystallography; Kynoch Press: Birmingham, UK, 1992; Vol. C).
31. For an alternative synthesis, see: Shono, T.; Kise, N.; Sanda, F.; Ohi, S.; Tsubata, K. Tetrahedron Lett. 1988, 29, 231.
32. Kobayashi, S.; Kamiyama, K.; Iimori, T.; Ohno, M. Tetrahedron Lett. 1984, 25, 2557.