Application of a new methodology for the synthesis of α-methyl- α-arylglycines using methyl acetamidoacrylate as an α-methylglycine cation equivalent

Arkivoc

Volumn 2005, Issue 6, 2005, Pages 46-61

  Royo, Elena ^a   López, Pilar ^a   Cativiela, Carlos ^a  

^a CSIC   (Spain)

Author keywords

aryl methylglycines; methylglycine cation; Chiral HPLC; Electrophilic aromatic substitution

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALPHA METHYL ALPHA (4 HYDROXYPHENYL)GLYCINE; ALPHA METHYL ALPHA (4 METHOXYPHENYL)GLYCINE; ANISOLE; CATION; GLYCINE DERIVATIVE; LEWIS ACID; PHENOL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRAL CHROMATOGRAPHY; DRUG SYNTHESIS; ENANTIOMER; FRIEDEL CRAFTS REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHODOLOGY; RACEMIC MIXTURE; REACTION ANALYSIS;

EID: 20044394085     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (56)

1. (a) Wagner, I.; Musso, H. Angew. Chem., Int. Ed. Engl. 1983, 22, 816.
2. (b) Hunt, S. In Chemistry and Biochemistry of the Amino Acids; Barrett, G. C., Ed.; Chapman and Hall: London, 1985, p 55.
3. Williams, R. M.; Hendrix, J. A. Chem. Rev. 1992, 92, 889.
4. For reviews about a-substituted a-amino acids and their properties see the following: (a) Seebach, D.; Sting, A. R.; Hoffmann, M. Angew. Chem., Int. Ed. Engl. 1996, 35, 2708.
5. (b) Wirth, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 225.
6. (c) Cativiela, C.; Díaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517.
7. Mossel, E.; Formaggio, F.; Crisma, M.; Toniolo, C.; Broxterman, Q. B.; Boesten, W. H. J.; Kamphuis, J.; Quaedflieg, P. J. L. M. Tetrahedron: Asymmetry 1997, 8, 1305.
8. Shuman, R. T.; Rothenberger, R. B.; Campbell, C. S.; Smith, G. F.; Gifford-Moore, D. S.; Paschal, J. W.; Gesellchen, P. D. J. Med. Chem. 1995, 38, 4446.
9. Stilz, H. U.; Beck, G.; Jablonka, B.; Just, M. Bull. Soc. Chim. Belg. 1996, 105, 711.
10. Conn, P. J.; Pin, J.-P. Annu. Rev. Pharmacol. Toxicol. 1997, 37, 205.
11. (a) Schoepp, D. D.; Jane, D. E.; Monn, J. A. Neuropharmacology 1999, 38, 1431.
12. (b) Watkins, J. C.; Krogsgaard-Larsen, P.; Honoré, T. Trends Pharmacol. Sci. 1990, 11, 25.
13. Watkins, J. C.; Collingridge, G. Trends Pharmacol. Sci. 1994, 15, 333.
14. (a) Hayashi, Y.; Sekiyama, N.; Nakanishi, S.; Jane, D. E.; Sunter, D. C.; Birse, E. F.; Udvarhelyi, P. M.; Watkins, J. C. J. Neurosci. 1994, 14, 3370.
15. (b) Sekiyama, N.; Hayashi, Y.; Nakanishi, S.; Jane, D. E.; Tse, H.-W.; Birse, E. F.; Watkins, J. C. Br. J. Pharmacol. 1996, 117, 1493.
16. (c) Conway, S. J.; Miller, J. C.; Howson, P. A.; Clark, B. P.; Jane, D. E. Bioorg. Med. Chem. Lett. 2001, 11, 777.
17. (a) Schöllkopf, U. Pure Appl. Chem. 1983, 55, 1799.
18. (b) Hartwig, W.; Schöllkopf, U. Liebigs Ann. Chem. 1984, 1952.
19. (c) Remuzon, P.; Soumeillant, M.; Dussy, C.; Bouzard, D. Tetrahedron 1997, 53, 17711.
20. (d) Ma, D.; Tian, H. Tetrahedron: Asymmetry 1996, 7, 1567.
21. (e) Ma, D.; Tian, H. J. Chem. Soc., Perkin Trans. 1 1997, 3493.
22. (f) Zdowsky, T. M.; de Lara, E.; Spaton, S. G. J. Org. Chem. 1990, 55, 5437.
23. (a) Ma, D.; Tian, H.; Zou, G. J. Org. Chem. 1999, 64, 120.
24. (b) Davies, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 65, 8704.
25. (a) Imogai, H.; Petit, Y.; Larchevêque, M. Tetrahedron Lett. 1996, 37, 2573.
26. (b) Matsushita, M.; Maeda, H.; Mitsuaki, K. Tetrahedron Lett. 1998, 39, 3749.
27. (a) O'Donnell, M. J.; Polt, R. L. J. Org. Chem. 1982, 47, 2663.
28. (b) Obrecht, D.; Bohdal, U.; Broger, C.; Bur, D.; Lehmann, C.; Ruffieux, R.; Schönholzer, P.; Spigler, C.; Müller, K. Helv. Chim. Acta 1995, 78, 563.
29. (a) Coudert, E.; Acher, F.; Azerad, R. Tetrahedron: Asymmetry 1996, 7, 2963.
30. (b) Ndzié, E.; Cardinael, P.; Schoofs, A.-R.; Coquerel, G. Tetrahedron: Asymmetry 1997, 8, 2913.
31. (a) Horikawa, H.; Nishitani, T.; Iwasaki, T.; Mushika, Y.; Inoue, I.; Miyoshi, M. Tetrahedron Lett. 1980, 21, 4101.
32. (b) Bueno, M. P.; Cativiela, C.; Finol, C.; Mayoral, J. A.; Jaime, C. Can. J. Chem. 1987, 65, 2182.
33. (c) Cativiela, C.; López, P.; Mayoral, J. A. Tetrahedron: Asymmetry 1991, 2, 1295.
34. (a) Horikawa, H.; Nishitani, T.; Iwasaki, T.; Inoue, I. Tetrahedron Lett. 1983, 24, 2193.
35. (b) Srivastava, V. P.; Roberts, M.; Holmes, T.; Stammer, C. H. J. Org. Chem. 1989, 54, 5866.
36. (c) Fernández, M. D.; De Frutos, M. P.; Marco, J. L.; Fernández-Alvarez, E.; Bernabé, M. Tetrahedron Lett. 1989, 30, 3101.
37. (a) Cardellicchio, C.; Fiandanese, V.; Marchese, G.; Naso, F.; Ronzini, L. Tetrahedron Lett. 1985, 26, 4387.
38. (b) Pérez, M.; Pleixats, R. Tetrahedron 1995, 51, 8355.
39. Cativiela, C.; López, M. P.; Mayoral, J. A. Synlett 1992, 121.
40. Roos, E. C.; Hiemstra, H.; Speckamp, W. N.; Kaptein, B.; Kamphuis, J.; Schoemaker, H. E. Synlett 1992, 451.
41. De la Hoz, A.; Díaz-Ortiz, A.; Gómez, M. V.; Mayoral, J. A.; Moreno, A.; Sánchez-Migallón, A. M.; Vázquez, E. Tetrahedron 2001, 57, 5421.
42. (a) Ben-Ishai, D.; Satati, I.; Berler, Z. J. Chem. Soc., Chem. Commun. 1975, 349.
43. (b) Ben-Ishai, D.; Satati, I.; Bernstein, Z. Tetrahedron 1976, 32, 1571.
44. Francotte, E. R. J. Chromatogr. A 2001, 906, 379.
45. (a) Dingenen, J. In A practical approach to chiral separations by liquid chromatography, Subramanian, G., Ed.; VCH Verlagsgesellschaft: Weinheim, 1994, p 115.
46. (b) Yashima, E.; Yamamoto, C.; Okamoto, Y. Synlett 1998, 344.
47. (a) Franco, P.; Senso, A.; Minguillón, C.; Oliveros, L. J. Chrom., A 1998, A 796, 265.
48. (b) Oliveros, L.; Lopez, P.; Minguillón, C.; Franco, P. J. Liq. Chrom. 1995, 18, 1521.
49. (a) Cativiela, C.; Díaz-de-Villegas, M. D.; Jiménez, A. I.; López, P.; Marraud, M.; Oliveros, L. Chirality, 1999, 11, 583.
50. (b) Alías, M.; Cativiela, C.; Jiménez, A. I.; López, P.; Oliveros, L.; Marraud, M. Chirality, 2001, 13, 48.
51. (c) Jiménez, A. I.; López, P.; Oliveros, L.; Cativiela, C. Tetrahedron 2001, 57, 6019.
52. (d) Royo, S.; López, P.; Jiménez, A. I.; Oliveros, L.; Cativiela, C. Chirality, 2002, 14, 39.
53. (e) Cativiela, C.; López, P.; Lasa, M. Eur. J. Org. Chem. 2004, 3898.
54. (a) Gil, A. M.; Buñuel, E.; López, P.; Cativiela, C. Tetrahedron: Asymmetry 2004, 2, 1295.
55. (b) Jiménez, A. I.; López, P.; Cativiela, C. Chirality, 2005, 17, 22.
56. (c) Gil, A. M.; López, P.; Buñuel, E.; Cativiela, C. ARKIVOC 2005, ix, 90.