A straightforward synthesis of both enantiomers of α-vinylalanine and α-ethynylalanine

Tetrahedron Asymmetry

Volumn 10, Issue 23, 1999, Pages 4653-4661

  Avenoza, Alberto ^a   Cativiela, Carlos ^b   Peregrina, Jesús M ^a   Sucunza, David ^a   Zurbano, María M ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b Instituto de Nanociencia y Materiales de Aragón   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE DERIVATIVE; ALPHA ETHYNYLALANINE; ALPHA VINYLALANINE; UNCLASSIFIED DRUG;

AMINO ACID SYNTHESIS; ARTICLE; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTEIN CONFORMATION; SPAIN;

EID: 0033377112     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00533-9     Document Type: Article

References (46)

1. (a) Mossel, E.; Formaggio, F.; Toniolo, C.; Crisma, M.; Boesten, W. H. J.; Broxterman, Q. B.; Kamphuis, J.; Quaedflieg, P. J.; Temussi, P. Tetrahedron: Asymmetry 1997, 8, 1305, and references cited therein
2. (b) Bellier, B.; McCort-Tranchenpain, I.; Ducos, B.; Danascimento, S.; Meudal, H.; Noble, F.; Garbay, C.; Roques, B. P. J. Med. Chem. 1997, 40, 3947.
3. (a) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708.
4. (b) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
5. Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
6. (a) Rando, R. R. Biochemistry 1974, 13, 3859.
7. (b) Metcalf, B. W.; Jund, K. Tetrahedron Lett. 1977, 41, 3689.
8. (a) Maycock, A. L.; Aster, S. D.; Patchett, A. A. Developments in Biochemistry 1979, 6, 115.
9. (b) Danzin, C.; Casara, P.; Claverie, N.; Metcalf, B. W. J. Med. Chem. 1981, 24, 16.
10. (c) Tendler, S. J. B.; Threadgill, M. D.; Tisdale, M. J. J. Chem. Soc., Perkin Trans. 1 1987, 2617.
11. Altmann, E.; Nebel, K.; Mutter, M. Helv. Chim. Acta 1991, 74, 800, and references cited therein.
12. (a) Walsh, C. Enzymatic Reaction Mechanisms; W. H. Freeman: San Francisco, 1979.
13. (b) Kuroda, Y.; Okuhara, M.; Goto, T.; Iguchi, E.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1980, 125.
14. (c) Kuroda, Y.; Okuhara, M.; Goto, T.; Iguchi, E.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiot. 1980, 132.
15. (a) Steglich, W.; Wegmann, H. Synthesis 1980, 481.
16. (b) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966.
17. (c) Aurell, M. J.; Gil, S.; Martínez, P. V.; Parra, M.; Tortajada, A.; Mestres, R. Synth. Commun. 1991, 21, 1833.
18. (a) Resolution of (±)-5-methyl-5-vinylhydantoin: Takamura, N.; Terashima, S.; Achiwa, K.; Yamada, S. Chem. Pharm. Bull. 1967, 15, 1776.
19. (b) Asymmetric α-methylation of vinyl substituted imidazolidinone: Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365.
20. (c) Combination of β-lactam synthesis by photolysis of oxazolidine carbene complex with Ojima's α-alkylation chemistry: Hegedus, L. S.; Colson, P. J. J. Org. Chem. 1993, 58, 5981.
21. (d) Synthesis of α-vinylalanine via lipase-mediated 'reverse transesterification'; Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743.
22. (a) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864.
23. (b) Schöllkopf, U.; Westphalen, K.-O.; Schröder, J.; Horn, K. Liebigs Ann. Chem. 1988, 781.
24. (a) Avenoza, A.; Cativiela, C.; Díaz-de-Villegas, M. D.; Mayoral, J. A.; Peregrina, J. M. Tetrahedron 1993, 49, 677.
25. (b) Avenoza, A.; Cativiela, C.; Díaz-de-Villegas, M. D.; Peregrina, J. M. Tetrahedron 1993, 49, 10987.
26. (c) Avenoza, A.; Cativiela, C.; París, M.; Peregrina, J. M. J. Org. Chem. 1994, 59, 7774.
27. (d) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M. Tetrahedron Lett. 1995, 36, 7123.
28. (e) Aubry, A.; Avenoza, A.; Cativiela, C.; Jiménez, A. I.; Marraud, M.; París, M.; Peregrina, J. M. Tetrahedron Lett. 1998, 39, 7841.
29. (f) Avenoza, A.; Busto, J. H.; Cativiela, C.; Peregrina, J. M.; Rodríguez, F. Tetrahedron 1998, 54, 11659.
30. Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220.
31. (a) Moriwake, T.; Hamano, S. I.; Saito, S.; Torii, S. Chem. Lett. 1987, 2085.
32. (b) McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31.
33. (a) Williams, L.; Zhang, Z.; Shao, F.; Carroll, P. J.; Joullié, M. M. Tetrahedron 1996, 52, 11673.
34. (b) Williams, L.; East, S. P.; Shao, F.; Joullié, M. M. Tetrahedron 1998, 54, 13371.
35. (a) Kobayashi, S.; Hachiya, I.; Araki, M.; Ishitani, H. Tetrahedron Lett. 1993, 34, 3755.
36. (b) Kobayashi, S.; Oriyama, T.; Noda, K. Synlett. 1998, 1047.
37. Beaulieu, P. L.; Duceppe, J.-S.; Johnson, C. J. Org. Chem. 1991, 56, 4196.
38. (a) Meffre, P.; Gauzy, L.; Perdigues, C.; Desanges-Levecque, F.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron Lett. 1995, 36, 877.
39. (b) Meffre, P.; Gauzy, L.; Branquet, E.; Durand, P.; Le Goffic, F. Tetrahedron 1996, 52, 11215.
40. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972, 3769.
41. Meffre, P.; Branquet, E.; Durand, P.; Le Goffic, F. Synth. Commun. 1998, 28, 613.
42. (a) Reginato, G.; Mordini, A.; Caracciolo, M. J. Org. Chem. 1997, 62, 6187.
43. (b) Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1994, 35, 3529.
44. McIntosh, M. C.; Weinreb, S. M. J. Org. Chem. 1993, 58, 4823.
45. (a) Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
46. (b) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.