Asymmetric diels-alder cycloaddition of 1-aminocyclohexadiene to chiral acrylate: Synthesis of enantiopure bridgehead-aminobicyclo[2.2.2]octane-2- carboxylic acid derivatives

European Journal of Organic Chemistry

Volumn , Issue 19, 2007, Pages 3166-3172

  Songis, Olivier ^a   Didierjean, Claude ^b   Laurent, Camille ^a   Martinez, Jean ^a   Calmès, Monique ^a  

^a UNIVERSITÉ DE MONTPELLIER   (France)

^b Nancy University CNRS   (France)

Author keywords

Asymmetric synthesis; Bicyclic amino acids; Chiral auxiliaries; Diels Alder reactions; Microwave activation

Indexed keywords

EID: 34447316201     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700236     Document Type: Article

References (42)

1. a) C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 1998, 9, 3517-3599;
2. b) C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 2000, 11, 645-732;
3. c) F. Fülöp, Chem. Rev. 2001, 101, 2181-2204;
4. d) K.-H. Park, M. J. Kurth, Tetrahedron 2002, 58, 8629-8659, and references cited therein.
5. For examples of the application of constrained α-amino acids, see: a) S. E. Gilson, N. Guillo, M. J. Tozer, Tetrahedron 1999, 55, 585-615;
6. b) C. Gallopini, S. Meini, M. Tancredi, A. Di Fenza, A. Triolo, L. Quartara, C. A. Maggi, F. Formaggio, C. Toniolo, S. Mazzucco, A. Papini, P. Rovero, J. Med. Chem. 1999, 42, 409-414;
7. c) P. Rovero, M. Pellegrini, A. Di Fenza, S. Meini, L. Quartara, C. A. Maggi, F. Formaggio, C. Toniolo, D. F. Mierke, J. Med. Chem. 2001, 44, 274-278.
8. For examples of the application of constrained β-amino acids, see: a) Y. Hayashi, J. Katade, T. Harada, K. Tachiki, Y. Takiguchi, M. Maramatsu, H. Miyazaki, T. Asari, T. Okazaki, Y. Dato, E. Yasuda, M. Tano, I. Uno, I. Ojima, J. Med. Chem. 1998, 41, 2345-2360;
9. b) S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180;
10. c) P. Furet, C. Garcia-Echeverria, B. Gay, J. Schoepfer, M. Zeller, J. Rahuel, J. Med. Chem. 1999, 42, 2358-2363;
11. d) P. G. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 2001, 101, 3219-3232;
12. e) B. Bellier, C. Garbay, Eur. J. Med. Chem. 2003, 38, 671-686;
13. f) M. Sukopp, R. Schwab, L. Marinelli, E. Biron, M. Heller, E. Varkondi, A. Pap, E. Novellino, G. Kéri, H. Kessler, J. Med. Chem. 2005, 48, 2916-2926;
14. g) F. Fülöp, T. A. Martinek, G. K. Toth, Chem. Soc. Rev. 2006, 35, 323-334.
15. a) J. D. Roberts, W. T. Moreland, W. Frazer, J. Am. Chem. Soc. 1953, 75, 637-640;
16. b) C. M. Wynn, W. R. Vaughan, J. Org. Chem. 1968, 33, 2371-2374;
17. c) A. C. Braisted, P. G. Schultz, J. Am. Chem. Soc. 1990, 112, 7430-7431;
18. d) R. Chinchilla, L. R. Falvello, N. Galindo, C. Najera. Tetrahedron: Asymmetry 1999, 10, 821-825;
19. e) R. Chinchilla, L. R. Falvello, N. Galindo, C. Najera, J. Org. Chem. 2000, 65, 3034-3041;
20. f) R. C. Reynolds, C. A. Johnson, J. R. Piper, F. M. Sirotnak, Eur. J. Med. Chem. 2001, 36, 237-242;
21. g) D. Arad, A. S. Kende, J. Lan, Tetrahedron Lett. 2002, 43, 5237-5239.
22. R. Zand, O. Z. Sellinger, R. Water, R. Harris, J. Neurochem. 1974, 23, 1201-1206.
23. P. W. Smith, N. Trivedi, P. D. Howes, S. L. Sollis, G. Rahim, R. C. Bethell, S. Lynn, Bioorg. Med. Chem. Lett. 1999, 9, 611-614.
24. V. E. Gouverneur, K. N. Houk, B. Pascal-Teresa, B. Beno, K. D. Janda, R. A. Lerner, Science 1993, 262, 204-208.
25. a) R. Akkari, M. Calmès, J. Martinez, Eur. J. Org. Chem. 2004, 2441-2450;
26. b) R. Akkari, M. Calmès, F. Escale, J. Iapichella, M. Rolland, J. Martinez, Tetrahedron: Asymmetry 2004, 15, 2515-2525;
27. c) M. Calmès, C. Didierjean, J. Martinez, O. Songis, Tetrahedron: Asymmetry 2005, 15, 2173-2178.
28. K. Gademann, T. Hintermann, J. V. Scheiber, Curr. Med. Chem. 1999, 6, 905-925, and references cited therein.
29. H. Graden, J. Hallberg, N. Kann, J. Comb. Chem. 2004, 6, 783-788.
30. a) W. Carruthers in Tetrahedron Organic Chemistry Series. Cycloaddition Reaction in Organic Synthesis, Pergamon Press, Oxford, 1990, vol. 8;
31. b) S. Kobayashi, K. A. Jorgensen, Cycloaddition reactions in organic synthesis, Wiley-VCH, Weinheim, 2002;
32. c) F. Fringuelli, A. Tatichi, The Diels-Alder Reaction: Selected Practical Methods; John Wiley & Sons, New York, 2002, and references cited therein.
33. A further problem with the use of Lewis acids is their possible complexation with both the two starting materials and the Diels-Alder products when a large quantity of the Lewis acid is required.
34. V. K. Aggarwal, A. Patin, S. Tisserand, Org. Lett. 2005, 7, 2555-2557.
35. T. Imamoto, Lanthanides in organic synthesis, Academic Press, London, 1994, and references cited therein.
36. a) J. P. Tierney, P. Lidström (Eds.), Microwave-assisted organic synthesis, Backwell Scientific, Oxford, 2004;
37. b) C. O. Kappe, A. Stadler, Microwaves in organic and medicinal chemistry, Wiley-VCH, Weinheim, 2005, vol. 25;
38. c) A. Loupy, Microwaves in organic synthesis, Wiley-VCH, Weinheim, 2005, vols. 1 and 2, and references cited therein.
39. Three of the four cycloadducts were separable using an achiral stationary phase and the ratio of the four cycloadducts was accurately determined by HPLC analyses using a chiracel OD column as a chiral stationary phase.
40. 2 = 0.0803 for reflections with I>2σ (I). CCDC-640598 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
41. HPLC data for the minor diastereoisomers 9 and 10 were deduced from a comparison of the HPLC profile of the crude diastereoisomeric mixtures with those of enantiopure compounds. It can be assumed that the endo approach at the Cα Re face of the dienophile was also favoured, which allowed us to assign the stereochemistry of compounds 9 and 10. This was supported by the rac-4/rac-5 ratio of 67:33 obtained after removal of the chiral auxiliary from a 30:60:3:7 mixture of compounds 7/8/9/10.
42. HPLC data for the minor diastereoisomers rac-9 and rac-10 were deduced from a comparison of the HPLC profile of racemic mixtures with those of diastereoisomeric mixtures.