α,γ-diamino acids: Asymmetric synthesis of new constrained 6-amino-3-azabicyclo[3.2.1]octane-6-carboxylic acids

Journal of Organic Chemistry

Volumn 71, Issue 22, 2006, Pages 8467-8472

  Caputo, Francesco ^a   Cattaneo, Cristian ^a   Clerici, Francesca ^a   Gelmi, Maria Luisa ^a   Pellegrino, Sara ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACIDS; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ASYMMETRIC SYNTHESIS; CHIRAL BUILDING BLOCKS; STERICAL CONSTRAINTS;

AMINO ACIDS;

6 AMINO 3 (4 METHOXYBENZYL) 3 AZABICYCLO[3.2.1]OCTANE 6 CARBOXYLIC ACID; 6 AMINO 3 AZABICYCLO[3.2.1]OCTANE 6 CARBOXYLIC ACID; ALPHA GAMMA DIAMINO ACID; CARBOXYLIC ACID DERIVATIVE; DIAMINO ACID; NORBORNENE DERIVATIVE; OCTANE; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; AMINO ACID SYNTHESIS; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOSELECTIVITY; STEREOSPECIFICITY; SUBSTITUTION REACTION;

AMINO ACIDS, DIAMINO; BICYCLO COMPOUNDS, HETEROCYCLIC; CARBOXYLIC ACIDS; MOLECULAR STRUCTURE; NORBORNANES; STEREOISOMERISM; TIME FACTORS;

EID: 33750428967     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061391o     Document Type: Article

References (37)

1. (a) Heng, R.; Revesz, L.; Schlapbach, A.; Waelchli, R. PCT Int. Appl. 2005, PIXXD2 WO 2005103054 A2 20051103; Chem. Abstr. 2005, 143, 440438.
2. (b) Hamamoto, I.; Takahashi, J.; Yano, M.; Hanai, D.; Iwasa, T. PCT Int. Appl. 2005, PIXXD2 WO 2005095380 A1 20051013; Chem. Abstr. 2005, 143, 386926.
3. (c) Evertsson, E.; Inghardt, T.; Lindberg, J.; Linusson, A.; Giordanetto, F. PCT Int. Appl. 2005, PIXXD2 WO 2005066132 A1 20050721; Chem. Abstr. 2005, 143, 172772.
4. (d) Breining, S. R.; Bhatti, B. S.; Hawkins, G. D.; Miao, L.; Anatoly, P.; Teresa, Y.; Miller, C. H. PCT Int. Appl. 2005, PIXXD2 WO 2005037832 A2 20050428; Chem. Abstr. 2005, 142, 430157.
5. (e) Dong, J.; Han, H.; Geng, B.; Li, X.; Gong, Z.; Liu, K. J. Peptide Res. 2005, 65, 440-444.
6. (f) Coe, J. W.; Iredale, P. A.; McHardy, S. F.; McLean, S. U.S. Patent Appl. Publ. 2005, USXXCO US 2005043345 A1; Chem. Abstr. 2005, 142, 233377.
7. (g) Bridger, G.; McEachern, E. J.; Skerlj, R.; Schols, D. U.S. Patent Appl. Publ. 2004, USXXCO US 2004209921 A1 20041021; Chem. Abstr. 2004, 141, 379809.
8. (h) Lew, W.; Wu, H.; Chen, X.; Graves, B. J.; Escarpe, P. A.; MacArthur, H. L.; Mendel, D. B.; Kim, C. U. Bioorg. Med. Chem. Lett. 2000, 10, 1257-1260.
9. (i) Yamashita, A.; Takahashi, N.; Mochizuki, D.; Tsujita, R.; Yamada, S.; Kawakubo, H.; Suzuki, Y.; Watanabe, H. Bioorg. Med. Chem. Lett. 1997, 7, 2303-2306.
10. (j) Takahashi, N.; Mochizuki, D. U.S. Patent Appl. USXXAMUS 5658923A 19970819, 1997; Chem. Abstr. 1997, 127, 248269.
11. (k) Rico, B.; Galvez, E.; Izquierdo, M. L.; Arias, M. S.; Orjales, A.; Berisa, A.; Labeaga, L. J. Heterocycl. Chem. 1994, 31, 313-318.
12. (l) Keasling, H. H.; Moffett, R. B. J. Med. Chem. 1971, 14, 1106-1112.
13. (a) Butora, G.; Goble, S. D.; Pasternak. A.; Yang, L.; Zhou, C.; Moyes, C. R. PCT Int. Appl. 2004, PIXXD2 WO 2004094371 A2 20041104; Chem. Abstr. 2004, 141, 410822.
14. (b) Chandrakumar, N. S.; Chen, B. B.; Clare, M.; Desai, B. N.; Djuric, S. W.; Docter, S. H.; Gasiecki, A. F.; Haack, R. A.; Liang, C.-D. PCT Int. Appl. 1996. PIXXD2 WO 9611192 A1 19960418; Chem. Abstr. 1996, 125, 142545.
15. (c) Buckley, B. R.; Page, P. C. B.; Heaney, H.; Sampler, E. P.; Carley, S.; Brocke, C.; Brimble, M. A. Tetrahedron 2005, 61, 5876-5888.
16. (d) Brocke, C.; Brimble, M. A.; Lin, D. S.-H.; McLeod, M. D. Synlett 2004, 13, 2359-2363.
17. (e) House, H. O.; Mueller, H. C. J. Org. Chem. 1962, 27, 4436-4439.
18. (f) Lowe, J. A., III; Drozda, S. E.; McLean, S.; Bryce, D. K.; Crawford, R. T.; Snider, R. M.; Longo, K. P.; Nagahisa, A.; Tsuchiya, M. J. Med. Chem. 1994, 37, 2831-2840.
19. (g) King, F. D. PCT Int. Appl. 1992, PIXXD2 WO 9212149 A1 19920723; Chem. Abstr. 1992, 117, 212337.
20. (a) Caputo, F.; Clerici, F.; Gelmi, M. L.; Nava, D.; Pellegrino, S. Tetrahedron 2006, 62, 1288-1294 and references therein.
21. (b) Caputo, F.; Clerici, F.; Gelmi, M. L.; Pellegrino, S.; Pocar, D. Tetrahedron: Asvmmetry 2006, 17, 1430-1436.
22. (a) Gelmi, M. L.; Pocar, D. Org. Prep. Proc. Int. 2003, 35, 141-205.
23. (b) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
24. (c) Advances in Amino Acids Mimetics and Peptido-mimetics; Abell, A., Ed.; JAI Press Inc.: London, UK, 1998.
25. (a) Trabocchi, A.; Guarna, F.; Guarna, A. Curr. Org. Chem. 2005, 9, 1127-1153.
26. (b) Baldauf, C.; Gunther, R.; Hofmann, H.-G. J. Org. Chem. 2004, 69, 6214-6220.
27. (c) Kimmerlin, T.; Seebach, D. J. Peptide Res. 2005, 65, 229-260.
28. (d) Ispida, H.; Kyakuno, M.; Oishi, S. Biopolymers 2004, 76, 69-82.
29. (e) Lelais, G.; Seebach, D. Biopolymers 2004, 76, 206-243.
30. (f) Souers, A. J.; Ellman, J. A. Tetrahedron 2001, 57, 7431-7448.
31. (g) Peptidomimetic Protocols (methods in Molecular Medicine); Kazmierski, W. M., Ed.; Humana Press Inc.: Totowa, NJ, 1999.
32. (h) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.; Lubell, W. D. Tetrahedron 1997, 53, 12789-12854.
33. (i) Hruby, W.; Li G.; Haskell-Luevano, C.; Shenderovic, M. Biopolymers 1997, 43, 219-248.
34. (J) Humphrey, J. M.; Chamberlin, A. R. Chem. Rev. 1997, 97, 2243-2266.
35. Bueno, M. P.; Cativiela, C.; Finol, C.; Mayoral, J. A. Can. J. Chem. 1987, 65, 2182-2186.
36. Iriepa, I.; Madrid, A. I.; Morreale, A.; Gálvez, E.; Bellanato, J. J. Mol. Struct. 2003, 651-653, 585-591 and references therein.
37. Kim, D.-I.; Schweri, M. M.; Deutsch, H. M. J. Med. Chem. 2003, 46, 1456-1464.