Solid-phase synthesis of piperidines by N-acyliminium ion chemistry

European Journal of Organic Chemistry

Volumn , Issue 18, 2002, Pages 3133-3139

  Veerman, Johan J N ^a   Klein, Jasper ^a   Aben, René W M ^b   Scheeren, Hans W ^b   Kruse, Chris G ^c   Van Maarseveen, Jan H ^a   Rutjes, Floris P J T ^a,b   Hiemstra, Henk ^a  

^a UNIVERSITY OF AMSTERDAM   (Netherlands)

^b RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

^c Solvay Pharmaceuticals Inc   (Netherlands)

Author keywords

Benzotriazole; Cyclisation; N Acyliminium ion; Nitrogen heterocycles; Piperidines

Indexed keywords

BENZOTRIAZOLE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SOLID; SYNTHESIS;

EID: 0036740219     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200209)2002:18<3133::AID-EJOC3133>3.0.CO;2-H     Document Type: Article

References (37)

1. [1a] D. O'Hagan, Nat. Prod. Rep. 2000, 17, 435.
2. [1b] D. O'Hagan, Nat. Prod. Rep, 1997, 14, 637.
3. [1c] A. O. Plunkett, Nat. Prod. Rep. 1994, 11, 581.
4. P. S. Watson, B. Jiang, B. Scott, Org. Lett. 2000, 2, 3679.
5. M. Prashad, Adv. Synth. Cat. 2001, 379 and references cited therein.
6. O. Okitsu, R. Suzuki, S. Kobayashi, J. Org. Chem. 2001, 66, 809 and references cited therein.
7. [5a] D. Compère, C. Marazano, B. C. Das, J. Org. Chem. 1999, 64, 4528.
8. [5b] D. Flammia, M. Dukat, I. M. Damaj, B. Martin, R. A. Glennon, J. Med. Chem. 1999, 42, 3726.
9. S. Laschat, T. Dickner, Synthesis 2000, 13, 1781 and references cited therein.
10. [7a] W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817.
11. [7b] H. de Koning, W. N. Speckamp, Methods Org. Chem. (Houben-Weyl) 1995, vol. E21b, p. 1953.
12. [7c] H. Hiemstra, W. N. Speckamp, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, Oxford, 1991, vol. 2, p. 1047.
13. [7d] R. A. Volkmann, In Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, Oxford, 1991, vol. 1, p. 355.
14. [7e] W. N. Speckamp, H. Hiemstra, Tetrahedron 1985, 41, 4367.
15. [8a] M. G. Valverde, D. Dallinger, C. O. Kappe, Synlett 2001, 6, 741.
16. [8b] C. Vanier, A. Wagner, C. Mioskowski, Chem. Eur. J. 2001, 7, 2318.
17. [8c] J. H. van Maarseveen, W. J. N. Meester, J. J. N. Veerman, C. G. Kruse, P. H. H. Hermkens, F. P. J. T. Rutjes, H. Hiemstra, J. Chem. Soc., Perkin Trans. 1 2001, 994.
18. [8d] H. Wang, A. Ganessian, Org. Lett. 1999, 1, 1647.
19. [8e] J. J. N. Veerman, F. P. J. T. Rutjes, J. H. van Maarseveen, H. Hiemstra, Tetrahedron Lett. 1999, 40, 6079.
20. [8f] W. J. N. Meester, F. P. J. T. Rutjes, P. H. H. Hermkens, H. Hiemstra, Tetrahedron Lett. 1999, 40, 1601.
21. [8g] M. Eguchi, M. S. Lee, H. Nakanishi, M. Stasiak, S. Lovell, M. Kahn, J. Am. Chem. Soc. 1999, 121, 12204.
22. [8h] T. Vojkovský, A. Weichsel, M. Pátek, J. Org. Chem. 1998, 63, 3162.
23. For additions to resin-bound N-acylimines, see: S. Schunk, D. Enders, Org. Lett. 2001, 3, 3177.
24. [8b]
25. A. R. Katritzky, X. Lan, J. Z. Yang, O. V. Denisko, Chem. Rev. 1998, 98, 409.
26. Details on the synthesis of amino acetals 9a-e are published in the preceding article: R. W. M. Aben, H. W. Scheeren, Eur. J. Org. Chem. 2002, 0000-0000. ((002200))
27. For a 2-Bt-substituted pyrrolidine see: A. R. Katritzky, Z. S. Luo, Y. F. Fang, Tetrahedron Lett. 2000, 41, 9691.
28. [14a] For benzotriazole as a leaving group in N-acyliminium ion chemistry, see: A. R. Katritzky, Y. Fang, A. Silina, J. Org. Chem. 1999, 64, 7622.
29. [14b] A. R. Katrizky, A. V. Ignatchenko, H. Lang, J. Org. Chem. 1995, 60, 4002.
30. 2 in the presence of pTSA (cat.) for 15 min to provide a mixture of 16 and 17. Allyltrimethylsilane was then added, and the mixture was stirred at room temperature for 20 h. This yielded a mixture consisting mainly of 16 and 17 and a small amount of product 14. Presumably, allyltrimethylsilane is not stable to protic acids, making this an ineffective procedure. This result corresponds well with the findings of Shono et al. who observed the same when trying to couple a silyl enol ether to an enamide precursor using a protic acid: T. Shono, Y. Matsumura, K. Tsubata, J. Am. Chem. Soc. 1981, 103, 1172.
31. T. Shono, Y. Matsumura, K. Tsubata, J. Takata, Chem. Lett. 1981, 1121.
32. [14a], in which isopropenyl acetate could only be coupled in a low yield.
33. J. A. C. Romero, S. A. Tabacco, K. A. Woerpel, J. Am. Chem. Soc. 2000, 122, 168.
34. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923.
35. F. D. King, Tetrahedron Lett. 1983, 31, 3281.
36. H. Abe, H.-S. Kim, Y. Wataya, T. Harayama, Tetrahedron 2001, 7, 1213.
37. S. K. Armstrong, E. W. Collington, J. Stonehouse, S. Warren, J. Chem. Soc., Perkin. Trans. 1 1994, 2825.