A three-component reaction for diversity-oriented synthesis of polysubstituted piperidines: Solution and solid-phase optimization of the first tandem aza [4+2]/allylboration

Chemistry - A European Journal

Volumn 9, Issue 2, 2003, Pages 466-474

  Touré, Barry B ^a   Hoveyda, Hamid R ^a,b   Tailor, Jyoti ^a   Ulaczyk Lesanko, Agnieszka ^a   Hall, Dennis G ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b Néokimia Inc   (Canada)

Author keywords

Boron; Diastereo selectivity; Heterocycles; Multicomponent reactions; Solid phase synthesis

Indexed keywords

ALDEHYDES; CONDENSATION; HYDRAZINE; OPTIMIZATION; REACTION KINETICS;

ALLYLBORATION REACTIONS;

SYNTHESIS (CHEMICAL);

ALDEHYDE; BORON; HYDRAZINE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; POLYMERIZATION; REACTION ANALYSIS; SOLID; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037455241     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.200390049     Document Type: Article

References (50)

1. a) For recent reviews on multicomponent reactions, see: a) R. W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown, T. A. Keating, Acc. Chem. Res. 1996, 29, 123-131;
2. b) L. Weber, K. Illgen, M. Almstetter, Synlett 1999, 366-37;
3. c) A. Dömling, Comb. Chem. High Throughput Screening 1999, 1, 1;
4. d) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344; Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
5. d) A. Dömling, I. Ugi, Angew. Chem. 2000, 112, 3300-3344; Angew. Chem. Int. Ed. 2000, 39, 3168-3210;
6. e) H. Bienaymé, C. Hulme, G. Oddon, P. Schmitt, Chem. Eur. J. 2000, 6, 3321-3329;
7. f) I. Ugi, Pure Appl. Chem. 2001, 73,187-191.
8. a) S. L. Schreiber, Science 2000, 287, 1964-1969;
9. b) P. Arya, D. T. H. Chou, M.-G. Baek, Angew. Chem. 2001, 113, 351-358; Angew. Chem.Int. Ed. 2001, 40, 339-346.
10. b) P. Arya, D. T. H. Chou, M.-G. Baek, Angew. Chem. 2001, 113, 351-358; Angew. Chem.Int. Ed. 2001, 40, 339-346.
11. Dictionary of Alkaloids (Eds.: I. W. Southon, J. Buckingham), Chapman and Hall, London, UK, 1989.
12. A. A. Patchett, R. P. Narglund, Annu. Rep. Med. Chem. 2000, 35, 289-298.
13. P. A. Grieco, A. Bahsas. Tetrahedron Lett. 1988, 29, 5855-5858.
14. a) W. Maison, A. Lützen, M. Kosten, I. Schlemminger, O. Westerhoff, J. Martens, J. Chem. Soc. Perkin Trans. 1 1999, 3515;
15. b) W. Maison, A. Lützen, M. Kosten, I. Schlemminger, O. Westerhoff, W. Saak, J. Martens, J. Chem. Soc. Perkin Trans. 1 2000, 1867-1871;
16. c) E. González-Zamora, A. Fayol, M. Bois-Choussy, A. Chiaroni, J. Zhu, Chem, Commun. 2001, 1684-1685.
17. N. A. Petasis, I. A. Zavialov, J. Am. Chem. Soc. 1998, 120, 11798-11799.
18. a) J. E. Semple, T. D. Owens, K. Nguyen, O. E. Levy, Org. Lett. 2000, 2, 2769-2772;
19. b) L. Banfi, G. Guanti, R. Riva, Chem. Commun. 2000, 985-986;
20. c) T. D. Owens, E. J. Semple, Org. Lett. 2001, 3, 3301-3304;
21. d) L. Banfi, G. Guanti, R. Riva, A. Basso, E. Calcagno, Tetrahedron Lett. 2002. 43, 4067-4069.
22. For reviews on the synthesis of piperidine-containing natural products, including indolizidines, see: a) G. Casiraghi, F. Zanardi, G, Rassu, P. Spanu, Chem. Rev. 1995, 95, 1677-1716;
23. b) J. P. Michael. Nat. Prod. Rep. 1998, 571-594;
24. c) P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun. 1998, 633-640:
25. d) A. Mitchinson, A. Nadin, J. Chem. Soc. Perkin Trans. 1 1999, 2553-2581;
26. e) S. Laschat, T. Dickner, Synthesis 2000, 1781-1813.
27. J. Tailor, D. G. Hall, Org. Lett. 2000, 2, 3715-3718.
28. For reviews, see: a) D. L. Boger in Comprehensive Organic Synthesis, Vol. 5 (Ed.: L.A. Paquette, Series Eds.: B.M. Trost, I. Fleming), Pergamon, Elmsford, NY, 1991, pp. 451-512.
29. a) M. Vaultier, F. Truchet, B. Carboni, R. W. Hoffmann, I. Denne, Tetrahedron Lett. 1987, 28, 4169-4172;
30. b) P.-Y. Renard, J.-Y. Lallemand, Bull. Soc. Chim. Fr. 1996. 133, 143-249;
31. c) G. Ohanessian, Y. Six, J.-Y. Lallemand, Bull. Soc. Chim. Fr. 1996, 133, 1143-1148;
32. d) L. Garnier, B. Plunian, J. Mortier, M. Vaultier, Tetrahedron Lett. 1996, 37, 6699-6700;
33. e) P.-Y. Renard, J.-Y. Lallemand, Tetrahedron: Asymmetry 1996, 7. 2523-2524;
34. f) P.-Y. Renard, Y. Six, J.-Y. Lallemand. Tetrahedron Lett. 1997, 38, 6589-6590;
35. g) R. A. Batey, A. N. Thadani, A. J, Lough, Chem. Commun. 1999, 475-476;
36. h) Y. Six, J.-Y. Lallemand, Tetrahedron Lett. 1999, 40, 1295-1296.
37. For other examples of MCRs involving [4+2] cycloadditions see: a) K. Paulvannan, Tetrahedron Lett. 1999, 40, 1851-1854;
38. b) H. Neumann, A. Jacobi von Wangelin, D. Gördes, A. Spannenberg, M. Belier, J. Am. Chem. Soc. 2001, 123, 8398-8399;
39. c) P. Janvier, X. Sun, H. Bienaymé, J. Zhu, J. Am. Chem. Soc. 2002, 124, 2560-2567.
40. Y. Tamura, T. Tsugoshi, Y. Nakajima, Y. Kita. Synthesis 1984. 930-933.
41. A. Kamabuchi, T. Moriya, N. Miyaura, A. Suzuki, Synth. Comm. 1993, 23. 2851-2859.
42. R. W. Hoffmann, S. Dresely, Synthesis 1988, 103-106.
43. See Figures 3 and 4 and accompanying text in: U. Ragnarsson, Chem. Soc. Rev. 2001, 30, 205-213.
44. CCDC-145481 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.uk).
45. a) R. W. Hoffmann, D. Brückner, V. J. Gerusz. Heterocycles 2000, 52. 121-124;
46. b) R. W. Hoffmann, D. Brückner, New J. Chem. 2001, 25, 369-373.
47. For a review on allylboration chemistry, see: D. S. Matteson, Stereo-directed Synthesis with Organoboranes, Springer, Berlin, 1995, Chapter 7.
48. R. Beaudegnies, L. Ghosez, Tetrahedron: Asymmetry 1994, 5, 557-560.
49. The absolute stereochemistry of 11 was assigned tentatively on the basis of ref. [21].
50. H. R. Hoveyda, D. G. Hall, Org. Lett. 2001, 3, 3491-3494.