Utilization of industrial waste materials. Part 14.† Synthesis of -amino alcohols and thiols with a 2-azabicyclo[3.3.0]octane backbone and their application in enantioselective catalysis

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 16, 1999, Pages 2353-2365

  Kossenjans, Michael ^a   Soeberdt, Michael ^a   Wallbaum, Sabine ^a   Harms, Klaus ^a   Martens, Jürgen ^a   Aurich, Hans Günter ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001914846     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a902362c     Document Type: Article

References (65)

1. (a) R. Crossley, Tetrahedron, 1992, 48, 8155;
2. (b) J. Crosby, Tetrahedron, 1991,47, 4789;
3. H.-J. Federsei, Chem. Unserer Zeit, 1993, 27, 78;
4. Chirality in Industry: The Commercial Manufacture and Application of Optically Active Compounds, ed. A. N. Collins, G. N. Shelchake and J. Crosby, J. Wiley & Sons, Chichester, 1992.
5. A. C. Regan, J. Chem. Soc., Perkin Trans, l, 1998, 1151.
6. M. Kitamura, S. Suça, K. Kawai and R. Noyori, J. Am. Chem. Soc., 1986,108,6071.
7. For reviews, see: (a) K. Soai and S. Niwa, Chem. Rer., 1992,92, 833;
8. (b) R. Noyori and M. Kitamura, Ange: Chem., Int. Ed. Engl., 1991, 30,49;
9. R. M. Devant and H.-E. Radunz, Methods ofOrg. Chem., (Houben-Weyl), 4th edn., Stercoseleclive Synthesis, 1995, ed. G. Helmchen, R. W. Hoffmann, J. Mulzer and E. Schaumann, vol. 21b, p. 1314.
10. Considering the great number of publications dealing with the enantioselective dialkylzinc addition only a few are selected: (a) K. Soai, A. Ookawa, T. Kaba and K. Ogawa, J. Am. Chem. Soc., 1987,109, 7111;
11. (b) K. Soai and S. Niwa, Chem. Lett., 1989,481;
12. M. Yoshioka, T. Kawakita and M. Ohno, Tetrahedron Lett., 1989, 30, 1657;
13. H. Takahashi, T. Kawakita and M. Yoshioka, Tetrahedron Lett., 1989, 30, 7095;
14. (e) M. Watanabe, S. Araki, Y. Butsugan and M. Uemura, J. Org. Chem., 1991, 56, 2218;
15. (f) B. Schmidt and D. Seebach, Angew. Chem., Int. Ed. Engl., 1991, 30,99;
16. (g) M. Ishizaki, K. I. Fujita, M. Shimamoto and O. Hoshino, Tetrahedron: Asymmetry, 1994, 5, 411;
17. (h) E. Rijnberg, J. T. B. H. Jastrzebski, M. D. Janssen, J. Boersma and G. van Koten, Tetrahedron Lett., 1994, 35, 6521;
18. D. Seebach, A. K. Beck, B. Schmidt and Y. M. Wang, Tetrahedron, 1994, 50, 4363;
19. (J) T. Wirth, Tetrajiedron Lett., 1995, 36, 7849;
20. (k) T. Wirth, K. J. Kulicke and G. Fragale, Heir. Chim. Ada, 1996, 79, 1957;
21. E. Rijnberg, N. J. Hovestad, A. W. Kleij, J. T. B. H. Jastrzebski, H. Boersma, M. D. Janssen, A. L. Spek and G. van Koten, Organomelallics, 1997, 16, 2847;
22. W.-S. Huang, Q.-S. Hu and L. Pu, J. Org. Chem., 1998,63, 1364.
23. (a) H. G. Aurich, F. Biesemeier, M. Geiger and K. Harms, Liebigs AnnJRecl., 1997,423;
24. (b) H. G. Aurich and M. Soeberdt, Tetrahedron Lett., 1998, 39, 2553;
25. S. Wallbaum and J. Martens, Tetrahedron: Asymmetry, 1993,4,637;
26. K. Stingl and J. Martens, Liebigs Ann., 1994, 491;
27. (e) J. Eilers, J. Wilken and J. Martens, Tetrahedron: Asymmetry, 1996, 7, 2343;
28. (f) J. Wilken, C. Thorey, H. Gröger, D. Haase, W. Saak, S. Pohl, J. Muzart and J. Martens, Liebigs Ann.l Reel., 1997, 2133;
29. (g) J. Wilken, M. Kossenjans, H. Gröger and J. Martens, Tetrahedron: Asymmetry, 1997, 8, 2007;
30. (h) J. Wilken, H. Gröger, M. Kossenjans and J. Martens, Tetrahedron: Asymmetry, 1997,8,2761.
31. This paper is part 14 of our series concerning the studies of the utilization of industrial waste materials. For part 13 see: M. Kossenjans and J. Martens, Tetrahedron: Asymmetry, submitted
32. for publication; for part 12 see: J. Wilken, H. Gröger, M. Kossenjans and J. Martens, Tetrahedron: Asymmetry, 1997, 8, 2761. The synthesis of the ACE-inhibitor Ramipril is described in: V. Teetz, R. Geiger and H. Gaul, Tetrahedron Lett., 1984, 25, 4479 and H. Urbach and R. Henning, Heterocycles, 1989,28, 957.
33. S. Wallbaum, T. Mehler and J. Martens, Syntli. Commun., 1994, 24, 1381.
34. J. A. Racan and M. C. ClatTey, Heterocycles, 1995,41, 57.
35. (a) A. I. Meyers and L. E. Burgess, J. Org. Client., 1991, 56, 2294;
36. (b) L. E. Burgess and A. I. Meyers, J. Org. Client., 1992,57, 1656.
37. The stereochemical outcome of the condensation of 7-ketoester 12 with p-amino alcohols was previously described in the literature: see réf. 9 and 12.
38. M. D. Ennis, R. L. HofTman, N. B. Ghazal, D. W. Old and P. A. Mooney.J Org. Client., 1996, 61, 5813.
39. (a) F. Möller, Methoden der Organischen Chemie (Houben-Weyl), 4th edn, vol. 11/1: ed. E. Müller, Thieme Verlag Stuttgart, 1957, p. 311;
40. (b) M. C. Carre; J. P. Houmounou and P. Cauberre, Tetrahedron Lejt., 1985, 26, 3107;
41. J.-I. Yamada, M. Yumoto and Y. Yamamoto,'Tetrahedron Lett., 1989, 30, 4255;
42. M. Fujiwara, M. Imada, A. Baba and H. Matsuda, Tetrahedron Lett., 1989, 30, 739;
43. (e) M. Chini, P. Crotti and F. Macchia, Tetrahedron Lett., 1990, 31,4661.
44. (a) P. O'Brien and P. Poumellec, Tetrahedron Lett., 1996, 37, 5619;
45. (b) S. E. de Sousa and P. O'Brien, Tetrahedron Lett., 1997,38,4885;
46. S. E. de Sousa, P. O'Brien and P. Poumellec, Tetrahedron: Asymmetry, 1997,8,2613.
47. (a) B. E. Rossiter, M. Eguchi, G. Miao, N. M. Swingle, A. E. Hernândez, D. Vickers, E. Fluckiger, R. G. Patterson and K. V. Reddy, Tetrahedron Lett., 1993, 49, 965;
48. (b) N. M. Swingle, K. V. Reddy and B. E. Rossiter, Tetrahedron, 1994, 50, 4455;
49. C. Miao and B. E. Rossiter, J. Org. Client., 1995, 60, 8424.
50. (a) R. K. Dieter, B. Lagu, J. W. Dieter, N. Deo and W. T. Pennington, Synlett, 1990, 109;
51. (b) R. K. Dieter, N. Deo, B. Lagu and J.W. Dieter, J. Org. Chew., 1992,57, 1663.
52. (a) R. P. Hof, M. A. Poelert, N. C. M. W. Peper and R. M. Kellog, Tetrahedron: Asymmetry, 1994, 5, 31;
53. (b) J. Kang, J. W. Lee and J. I. Kirn, J. Client. Soc., Cheni. Commun., 1994, 2~009;
54. J. Kang, D. S. Kirn and J. I. Kirn, Synlett, 1994, 842;
55. K. Fitzpatrick, R. Hülst and R. M. Kellogg, Tetrahedron: Asymmetry, 1995, 6, 1861;
56. (e) C. L. Gibson, Client. Commun., 1996, 645;
57. (f) Y. Masaki, Y. Satoh, T. Makihara and M. Shi, Client. Pliarm. Bull., 1996, 44, 454.
58. A similar reaction has been described recently: D. A. Fulton and C. L. Gibson, Tetrahedron Lett., 1997,38, 2019.
59. P. Truitt, D. Mark, L. M. Lone and J. Jeans, J. Am. Client. Soc., 1948,70,4214.
60. R. P. Linstead and E. M. Meade, J. Client. Soc., 1934,935.
61. (a) M. C. Rebstock and A. C. Moore, J. Am. Client. Soc., 1953, 75, 1685;
62. (b) L. F. Tietze and T. Eicher, Reaktionen und Synthesen, 2. Aufl. 1991, p. 135, Thieme Verlag, Stuttgart;
63. A. Giannis and K. Sandhoff, Angeu: Client., Int. Ed. Engl, 1989, 28, 218;
64. A. Abiko and S. Masamune, Tetrahedron Lett., 1992,33, 5517.
65. R. H. Richard and J. Kenyon, J. Client. Soc., 1936, 128.