Synthesis of enantiopure functionalized pipecolic acids via amino acid derived N-acyliminium ions

European Journal of Organic Chemistry

Volumn , Issue 5, 1999, Pages 1127-1135

  Rutjes, Floris P J T ^a   Veerman, Johan J N ^a   Meester, Wim J N ^a   Hiemstra, Henk ^a   Schoemaker, Hans E ^b  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b DSM RESEARCH   (Netherlands)

Author keywords

Enzymatic resolution; N Acyliminium ions; Non natural amino acids; Pipecolic acid derivatives; Rearrangements

Indexed keywords

N ACYLIMINIUM DERIVATIVE; PIPECOLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VINYL SILANE DERIVATIVE;

AMINO ACID ANALYSIS; ARTICLE; CYCLIZATION; ENANTIOMER; REACTION ANALYSIS; REACTION TIME; SYNTHESIS;

EID: 0032783850     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199905)1999:5<1127::AID-EJOC1127>3.0.CO;2-A     Document Type: Article

References (59)

1. See for example: [1a] M. G. Moloney, Nat. Prod. Rep. 1998, 205-219.
2. [1b] B. Ho. T. M. Zabriskie, Bioorg. Med. Chem. Lett. 1998, 8, 739-744.
3. S. J. Mihalik, W. J. Rhead, J. Biol. Chem. 1989, 264, 2509.
4. [3a] F. E. King, T. J. King, A. J. Warwick, J. Chem. Soc. 1950, 3590-3597.
5. [3b] Y. Hasegawa, H. Hashimoto, M. Maeda, Agric. Biol. Chem. 1980, 44, 2725-2728.
6. [3c] N. A. Dobson, R. A. Raphael, J. Chem. Soc. 1985, 3642-3647.
7. [3d] A. W. Burgstahler, C. E. Aiman, J. Org. Chem. 1960, 25, 489-492.
8. [4a] J. T. Romeo, L. A. Swain, A. B. Bleecker, Phytochemistry 1983, 22, 1615.
9. [4b] H. Vanderhaeghe, G. Janssen, F. Compernolle, Tetrahedron Lett. 1971, 28, 268.
10. J. W. Clark-Lewis, P. I. Mortimer, J. Chem. Soc. 1961, 189.
11. [6a] A. S. Golubev, N. Sewald, K. Burger, Tetrahedron 1996, 47, 14757-14776.
12. [6b] H. Kessler, M. Kühn, T. Löschner, Liebigs Ann. Chem. 1986, 1-20.
13. [6c] J. W. Reed, M. B. Purvis, D. G. I. Kingston, A. Biot. F. Gosselé, J. Org. Chem. 1989, 54, 1161-1165.
14. See e.g.: A. J. Hutchison, M. Williams, C. Angst, R. de Jesus, L. Blanchard, R. H. Jackson, E. J. Wilusz, D. E. Murphy, P. S. Bernard, J. Schneider, T. Campbell, W. Guida, M. A. Sills, J. Med. Chem. 1989, 32, 2171.
15. P. L. Ornstein, D. D. Schoepp, M. B. Arnold, J. D. Leander, J. W. Paschal, T. Elzey, J. Med. Chem. 1991, 34, 90.
16. [9a] C. Herdeis, W. Engel, Arch. Pharm. (Weinheim, Ger.) 1993, 326, 297-301.
17. [9b] C. S. R. Angle, D. O. Arnaiz, Tetrahedron Lett. 1989, 30, 515-518.
18. [9c] J. J. N. Veerman, J. H. van Maarseveen, G. M. Visser, C. G. Kruse, H. E. Schoemaker, H. Hiemstra, F. P. J. T. Rutjes, Eur. J. Org. Chem., in press.
19. [10a] R. E. A. Callens, M. J. O. Anteunis, F. Reyniers, Bull. Soc. Chim. Belg. 1982, 91, 713-723.
20. [10b] A. P. Nin, O. Varela, R. M. de Lederkremer Tetrahedron 1993, 49, 9459.
21. [10c] G. J. Hanson, M. A. Russell, Tetrahedron Lett. 1989, 30, 5751-5754.
22. [10d] A. Golubev, N. Sewald, K. Burger, Tetrahedron Lett. 1995, 3, 33.
23. [10e] Y. Bousquet, P. C. Andersen, T. Bogri, J.-S. Duceppe, L. Grenier, I. Guse, Tetrahedron 1997, 53, 15671 - 15680.
24. [10f] F. P. J. T. Rutjes, H. E. Schoemaker, Tetrahedron Lett. 1997, 38, 677-680.
25. [10g] P. D. Bailey, G. R. Brown, F. Korber, A. Reed, R. D. Wilson, Tetrahedron: Asymmetry 1991, 2, 1263-1282.
26. [10h] R. F. W. Jackson, L. J. Graham, A. B. Rettie, Tetrahedron Lett. 1994, 35, 4417-4418.
27. [10i] R. Pellicciari, B. Natalini, R. Luneia, M. Marinozzi, M. Roberti, G. C. Rosato, B. M. Sadeghpour, J. P. Snyder, J. B. Monahan, F. Moroni, Med. Chem. Res. 1992, 2, 491.
28. [10j] Y. Fujita, J. Kollonitsch, B. Witkop, J. Am. Chem. Soc. 1965, 87, 2030.
29. For a racemic route, see: [11a] S. J. Hays, T. C. Malone, G. Johnson, J. Org. Chem. 1991, 56, 4084.
30. -For enantiopure approaches, see: [11b] C. Agami, F. Couty, M. Poursoulis, J. Vaissermann, Tetrahedron 1992, 48, 431.
31. [11c] J. Gillard, A. Abraham, P. C. Anderson, P. L. Beaulieu, T. Bogri, Y. Bousquet, L. Grenier, I. Guse, P. Lavallée, J. Org. Chem. 1996, 61, 2226-2231.
32. [11d] J. W. Skiles, P. P. Giannousis, K. R. Fales, Bioorg. Med. Chem. Lett. 1996, 6, 963-966.
33. For racemic routes, see: [12a] P. M. Esch, I. M. Boska, H. Hiemstra, W. N. Speckamp, Synlett 1989, 38.
34. [12b] P. M. Esch, I. M. Boska, H. Hiemstra, R. F. de Boer, W. N. Speckamp, Tetrahedron 1991, 47, 4039-4062.
35. [12c] P. M. Esch, R. F. de Boer, H. Hiemstra, I. M. Boska, W. N. Speckamp, Tetrahedron 1991, 47, 4063-4076.
36. -For enantiopure routes, see: [12d] C. Agami, C. Kadouri-Puchot, V. Le Guen, J. Vaissermann, Tetrahedron Lett. 1995, 36, 1657.
37. [12e] C. Agami, D. Bihan, L. Hamon, C. Kadouri-Puchot, M. Lusinchi, Eur. J. Org. Chem. 1998, 2461-2465.
38. For reviews on N-acyliminium ions, see: [13a] H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, 1. Fleming), Pergamon, Oxford, 1991, vol. 2, p. 1047.
39. [13b] H. de Koning, W. N. Speckamp, Methoden Org. Chem. (Houben-Weyl) 1995, vol. E 21b, p. 1953-2009.
40. [13c] H. Hiemstra, W. N. Speckamp in The Alkaloids, vol. 32 (Ed.: A. Brossi), Academic Press, Inc., San Diego, 1988, pp. 271-239.
41. [13d] H. de Koning, M. J. Moolenaar, H. Hiemstra, W. N. Speckamp in Studies in Natural Products Chemistry, vol. 13 (Ed.: Atta-ur-Rahman), Elsevier, Amsterdam, 1993, pp. 473-518.
42. For similar trapping experiments, see: D. J. Hart, Y.-M. Tsai, Tetrahedron Lett. 1981, 22, 1567.
43. [15a] G. W. Daub, D. A. Heerding, L. E. Overman, Tetrahedron 1988, 44, 3919-3930.
44. P. Castro, L. E. Overman, X. Zhang, P. S. Mariano, Tetrahedron Lett. 1993, 34, 5243-5246.
45. S. J. Veenstra, K. Hauser, W. Schilling, C. Betschart, S. Ofner, Bioorg. Med. Chem. Lett. 1996, 6, 3029-3034.
46. Q. B. Broxterman, B. Kaptein, J. Kamphuis, H. E. Schoemaker, J. Org. Chem. 1992, 57, 6286.
47. B. Kaptein, W. H. J. Boesten, Q. B. Broxterman, P. J. H. Peters, H. E. Schoemaker, J. Kamphuis, Tetrahedron: Asymmetry 1993, 4, 1113-1116.
48. [19a] M. J. O'Donnell, R. L. Polt, J. Org. Chem. 1982, 47, 2663-2666.
49. [19b] M. J. O'Donnell, K. Wojciechowski, L. Ghosez, M. Navarro, F. Sainte, J.-P. Antoine, Synthesis 1984, 313-315.
50. [20a] H. Hiemstra, W. J. Klaver, W. N. Speckamp, Recl. Trav. Chim. Pays-Bas 1986, 105, 299-306.
51. [20b] T. K. Jones, S. E. Denmark, Org. Synth. 1986, 64, 182-188.
52. [20c C. A. Brown, V. K. Ahuja, J. Org. Chem. 1973, 38, 2226-2230.
53. Obtained from DSM Research.
54. For reviews on this type of resolution, see: [22a] V. H. M. Elferink, D. Breitgoff, M. Kloosterman, J. Kamphuis, W. J. J. van den Tweel, E. M. Meijer, Recl. Trav. Chim. Pays-Bas 1991, 110, 63-74.
55. [22b] H. E. Schoemaker, W. H. J. Boesten, B. Kaptein, H. F. M. Hermes, T. Sonke, Q. B. Broxterman, W. J. J. van den Tweel, J. Kamphuis, Pure Appl. Chem. 1992, 64, 1171-1175.
56. [22c] H. E. Schoemaker, W. H. J. Boesten, B. Kaptein, E. C. Roos, Q. B. Broxterman, W. J. J. van den Tweel, J. Kamphuis, Acta Chem. Scand. 1996, 50, 225-233.
57. The ee values were determined by chiral HPLC analysis with a Crownpak (CR+) column according to a known procedure: Miyazawa, T.; Iwanaga, H.; Yamada, T.; Kuwata, S. Chem. Express 1991, 6, 887.
58. For a similar discussion with oxygen-stabilized cations, see: C. Semeyn, R. H. Blaauw, H. Hiemstra, W. N. Speckamp, J. Org. Chem. 1997, 62, 3426-3427 and references cited therein.
59. A. I. Vogel, A Textbook of Practical Organic Chemistry, 3rd ed., London, Longman, 1956, p. 971.