Deamination of the amino acid fragment in imine metallacycles: Unexpected synthesis of an NH-aldimine organometallic compound

Chemistry - A European Journal

Volumn 12, Issue 3, 2006, Pages 887-894

  Albert, Joan ^a   Cadena, J Magali ^a   González, Asensio ^a   Granell, Jaume ^a   Solans, Xavier ^a   Font Bardia, Mercè ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Aldiminejs; Amino acids; Deamination; Metallacycles; Palladium

Indexed keywords

ALDIMINEJS; DEAMINATION; METALLACYCLES; PALLADIUM ACETATE;

AMINES; AMINO ACIDS; ESTERS; PALLADIUM COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AMINATION;

ORGANOMETALLIC COMPOUND; PALLADIUM; PHENYLALANINE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHENYLALANINE;

EID: 30744455283     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200500099     Document Type: Article

References (65)

1. a) K. Severin, R. Bergs, W. Beck, Angew. Chem. 1998, 110, 1722-1743;
2. Angew. Chem. Int. Ed. 1998, 57, 1634-1654.
3. G. Jaouen, A. Vessiers, I. S. Butler, Acc. Chem. Res. 1993, 26, 361-369.
4. H. Chen, S. Ogo, R. H. Fish, J. Am. Chem. Soc. 1996, 118, 4993-5001.
5. a) A. Bohm, B. Schreiner, N. Steiner, R. Urban, K. Sünkel, K. Polborn, W. Beck, Z. Naturforsch. B 1998, 53, 191-205;
6. b) A. Bohm, K. Polborn, K. Sünkel, W. Beck, Z. Naturforsch. B 1998, 53, 448-458;
7. c) A. Bohm, K. Polborn, W. Beck, Z. Naturforsch. B 1999, 54, 300-305.
8. A. D. Ryabov, V. A. Polyakov, A. K. Yatsimirki, Inorg. Chim. Acta 1984, 91, 59-65.
9. Y. Fuchita, K. Yoshinaga, Y. Ikeda, J. Kinoshita-Kawashima, J. Chem. Soc. Dalton Trans. 1997, 2495-2500.
10. R. Grigg, J. Devlin, J. Chem. Soc. Chem. Commun. 1986, 631-632.
11. G. Giullena, G. Rodriguez, G. van Koten, Tetrahedron Lett. 2002, 43, 3895-3898.
12. J. Albert, J. M. Cadena, A. Gonzalez, J. Granell, X. Solans, M. Font-Bardia, J. Organomet. Chem. 2002, 663, 277-283.
13. For the synthesis of cyclopalladated compounds, see: a) M. I. Bruce, Angew. Chem. 1977, 89, 75-89;
14. Angew. Chem. Int. Ed. Engl. 1977, 16, 73-86;
15. b) G. R. Newkome, W. E. Puckett, V. K. Gupta, G. Kiefer, Chem. Rev. 1986, 86, 451-489;
16. c) I. Omae, Coord. Chem. Rev. 1988, 83, 137-167;
17. d) V. V. Dunina, O.A. Zalevskaya, V.M. Potapov, Russ. Chem. Rev. 1988, 57, 250-269;
18. e) A. D. Ryabov, Chem. Rev. 1990, 90, 403-424.
19. For some interesting reactions and applications of cyclopalladated compounds, see: a) M. Q. Slagt, G. Rodríguez, M. M. P. Grutters, R.J. M. Klein Gebbing, W. Klopper, L.W. Jenneskens, M. Lutz, A. L. Spek, G. Van Koten, Chem. Eur. J. 2004, 10, 1331-1344;
20. b) G. Rodriguez, M. Lutz, A. L. Sdpek, G. van Koten, Chem. Eur. J. 2002, 8, 46-57;
21. c) M. Ghedini, I. Aiello, A. Crsipini, M. La Deda, Dalton Trans. 2004, 1386-1392;
22. d) I. Aiello, D. Datillo, M. Ghedini, A. Golemme, J. Am. Chem. Soc. 2001, 123, 5598-5599;
23. e) A. W. Kleig, R. J. M. Klein Gebbing, P. A. J. van den Nieuwenhuijzen, H. Kooijman, M. Lutz, A. L. Spek, G. Van Koten, Organometallics 2001, 20, 634-647;
24. f) J. Vicente, I. Saura Llamas, J. Cuadrado, M. C. Ramirez de Arellano, Organometallics 2003, 22, 5513-5517;
25. g) J. Martínez, M. T. Pereira, I. Buceta, G. Alberdi, A. Amoedo, J. J. Fernández, M. López-Torres, J. M. Vila, Organometallics 2003, 22, 5581-5584;
26. h) M. Lopez-Torres, A. Fernández, J. J. Fernández, A. Suarez, S. Castro-Juiz, J. M. Vila, M. T. Pereira, Organometallics 2001, 20, 1350-1353;
27. i) J. Vicente, I. Saura Llamas, M. G. Palin, P. G. Jones, M. C. Ramirez de Arellano, Organometallics 1997, 16, 826-833;
28. j) A. D. Ryabov, Synthesis 1985, 233-252;
29. k) M. Pfeffer, Recl. Trav. Chim. Pays Bas 1990, 109, 567-576;
30. l) P. Espinet, M. A. Esteruelas, L. A. Oro, J. L. Serrano, E. Sola, Coord. Chem. Rev. 1992, 117, 215-274;
31. m) C. Navarro-Ranninger, I. López-Solera, J. M. Pérez, J. R. Masaguer, C. Alonso, Appl. Organomet. Chem. 1993, 7, 57-61;
32. n) M. Camargo, P. Dani, J. Dupont, R. F. de Souza, M. Pfeffer, I. Tkatchenko, J. Mol. Catal. A 1996, 709, 127-131;
33. o) R. Navarro, E. P. Urriolabeitia, C. Cativiela, M. D. Diaz de Villegas, M. P. López, E. Alonso, J. Mol Catal. A 1996, 105, 111-116.
34. A preliminary communication on the synthesis and characterization of the NH-aldirnine derivative has been published: J. Albert, J. M. Cadena, A. Gonzalez, J. Granell, X. Solans, M. Font Bardia, Chem. Commun. 2003, 528-529.
35. A. T. Nielson, R. L. Atkins, J. DiPol, D. W. Moore, J. Org. Chem. 1974, 39, 1349-1355.
36. J. C. Guillemin, J. M. Denis, Angew. Chem. 1982, 94, 715;
37. Angew. Chem. Int. Ed. Engl. 1982, 21, 690-691.
38. D. R. Boyd, P. B. Coulder, R. Hamilton, N. T. Thompson, N. D. Sharma, M. E. Stubbs, J. Chem. Soc. Perkin Trans. 1 1985, 2123-2127.
39. B. Bodganovic, M. Velic, Angew. Chem. 1967, 79, 818-819;
40. Angew. Chem. Int. Ed. Engl. 1967, 6, 803-804.
41. D. R. Boyd, R. Hamilton, N. T. Thompson, M. E. Stubbs, Tetrahedron Lett. 1979, 20, 3201-3204.
42. G. Chen, H. C. Brown, J. Am. Chem. Soc. 2000, 122, 4217-4218.
43. R. Cohen, B. Rybtchinski, M. Gandelman, L. J. W. Shimon, J. M. L. Martin, D. Milstein, Angew. Chem. 2003, 115, 1993-1996;
44. Angew. Chem. Int. Ed. 2003, 42, 1949-1952.
45. For a review, see: R. A. John, Biochim. Biophys. Acta 1995, 1248, 81-97.
46. C. G. McCarthy in The Chemistry of the Carbon-Nitrogen Double Bond (Ed.: S. Patai), Wiley, Chichester, 1970, pp. 364-372 and 405-408.
47. a) J. Albert, M. Gómez, J. Granell, J. Sales, X. Solans, Organometallics 1990, 9, 1405-1413;
48. b) J. Albert, J. Granell, J. Sales, M. Font-Bardia, X. Solans, Organometallics 1995, 14, 1393-1404.
49. a) J. Vicente, J. A. Abad, E. Martínez-Viviente, P. G. Jones, Organometallics 2002, 21, 4454-4462;
50. b) J. Vicente, A. Areas, D. Bautista, P. G. Jones, Organometallics 1997, 16, 2127-2138;
51. c) J. Vicente, J. A. Abad, A. D. Frankland, M. C. Ramirez de Arellano, Chem. Eur. J. 1999, 5, 3066-3075.
52. a) A. Crispini, M. Ghedini, J. Chem. Soc. Dalton Trans. 1997, 75-82;
53. b) G. De Munno, M. Ghedini, F. Neve, Inorg. Chim. Acta 1995, 259, 155-158.
54. Z. Hamersack, B. Peric, B. Kojic-Prodic, L. Cotarca, P. Delogu, V. Sunjic, Helv. Chim. Acta 1999, 82, 1289-1301.
55. O. Itoh, T. Nagata, I. Nomura, T. Takanaga, T. Sugita, K. Ichikawa, Bull Chem. Soc. Jpn. 1984, 57, 810-814.
56. T. Ohwada, K. Shudo, J. Org. Chem. 1989, 54, 5227-5237.
57. A. Rios, J. Crugeiras, T. L. Amyes, J. P. Richard, J. Am. Chem. Soc. 2001, 123, 7949-7950.
58. A. R. Battersby, D. G. Buckley, J. Staunton, P. J. Williams, J. Chem. Soc. Perkin Trans. 1 1979, 2550-2558.
59. Monoamine oxidases are primarily responsible for norepinephrine, serotonin, and dopamine metabolism and monoamine oxidase inhibitors are used as antidepressant agents (because depression has been associated with decreased functional amine-dependent synaptic transmission). See, for example : W. Z. Potter, L. E. Hollister in Basic and Clinical Pharmacology (Ed.: B. G. Katzung), Appleton & Lange, Connecticut, 1998, pp. 483-491.
60. C. E. Castro, M. Jamin, W. Yokoyama, R. Wade, J. Am. Chem. Soc. 1986, 108, 4179-4187.
61. See, for example: D. Sole, L. Vallverdú, X. Solans, M. Font-Bardia, J. Bonjoch, Organometallics 2004, 23, 1438-1447;
62. J. Vicente, J. A. Abad, W. Förstch, P. G. Jones, A. K. Fischer, Organometallics 2001, 20, 2704-2715;
63. R. Bosque, C. López, Polyhedron 1999, 18, 135-143.
64. G. M. Sheldrick, A computer program for determination of crystal structure, University of Göttingen, Germany, 1997.
65. International Tables of X-Ray Crystallography, Vol. IV, Kynoch Press, Birmingham, UK, 1974, pp. 99-100 and 149.