Stereoselective synthesis of highly substituted piperidines

European Journal of Organic Chemistry

Volumn , Issue 12, 1999, Pages 3353-3362

  Schneider, Christoph ^a   Börner, Christoph ^a   Schuffenhauer, Ansgar ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Aza conjugate addition; Cope rearrangement; Imines; Natural products; Piperidines

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DRUG CONFORMATION; DRUG SYNTHESIS; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0344210439     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199912)1999:12<3353::aid-ejoc3353>3.0.co;2-q     Document Type: Article

References (50)

1. [1a] G. M. Strunz, J. A. Findlay The Alkaloids, Academic Press, New York, 1985, 26, 89; A. R. Pinder Nat. Prod. Rep. 1993, 10, 491.
2. [1a] G. M. Strunz, J. A. Findlay The Alkaloids, Academic Press, New York, 1985, 26, 89; A. R. Pinder Nat. Prod. Rep. 1993, 10, 491.
3. [1b] I. W. Southon, J. Buckingham Dictionary of Alkaloids, Chapman and Hall, London, 1989.
4. Recent reviews: [2a] P. D. Bailey, P. A. Millwood, P. D. Smith, Chem. Commun. 1998, 633-640.
5. [2b] F. J. Sardina, H. Rapoport, Chem. Rev. 1996, 96, 1825-1849.
6. [3a] P. A. Grieco, S. D. Larsen, J. Am. Chem. Soc. 1985, 107, 1768-1769.
7. [3b] M. M. Midland, J. I. McLoughlin, Tetrahedron Lett. 1988, 29, 4653-4656.
8. [3c] H. Kunz, W. Pfrengle, Angew. Chem. Int. Ed. Engl. 1989, 28, 1067-1068.
9. [3d] H. Waldmann, M. Braun, M. Dräger, Angew. Chem. Int. Ed. Engl. 1990, 29, 1468-1470.
10. [3e] M. M. Midland, R. W. Koops, J. Org. Chem. 1992, 57, 1158-1161.
11. [3f] K. Ishihara, M. Miyata, K. Hattori, T. Tada, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 10520-10524;
12. [3g] S. Kobayashi, S. Komiyama, H. Ishitani, Angew. Chem. Int. Ed. 1998, 37, 979-981.
13. [3h] S. Yao, M. Johannsen, R. G. Hazell, K. A. Jorgensen, Angew. Chem. Int. Ed. 1998, 37, 3119-3122.
14. [3i] S. C. Schürer, S. Blechert, Tetrahedron Lett. 1999, 40, 1877-1880.
15. [4a] C. Flann, T. C. Malone, L. E. Overman, J. Am. Chem. Soc. 1987, 109, 6097-6107.
16. [4b] L. F. Tietze, M. Bratz, Chem. Ber. 1989, 122, 997-1002.
17. [4c] L. E. Overman, A. K. Sarkar, Tetrahedron Lett. 1992, 33, 4103-4106.
18. [4d] P. Castro, L. E. Overman, X. Zhang, P. S. Mariano, Tetrahedron Lett. 1993, 34, 5243-5246.
19. [4e] N. deKimpe, M. Boelens, J. Piqueur, J. Baele, Tetrahedron Lett. 1994, 35, 1925-1928.
20. [4f] T.-K. Yang, T.-F. Teng, J.-Y. Lin, Y.-Y. Lay, Tetrahedron Lett. 1994, 35, 3581-3582.
21. [4g] S. Laschat, R. Fröhlich, B. Wibbeling, J. Org. Chem. 1996, 61, 2829-2838.
22. [5a] R. Yamaguchi, M. Moriyasu, M. Yoshioka, M. Kawanisi, J. Org. Chem. 1988, 53, 3507-3512.
23. [5b] D. L. Comins, M. O. Killpack, J. Am. Chem. Soc. 1992, 114, 10973-10974.
24. [5c] D. L. Comins, S. P. Joseph, R. R. Goehring, J. Am. Chem. Soc. 1994, 116, 4719-4728.
25. [6a] L. Guerrier, J. Royer, D. S. Grierson, H.-P. Husson, J. Am. Chem. Soc. 1983, 105, 7754-7755.
26. [6b] M. Bonin, D. S. Grierson, J. Royer, H.-P. Husson, Org. Synth. 1991, 70, 54.
27. [6c] M. Amat, N. Llor, J. Bosch, Tetrahedron Lett. 1994, 35, 2223-2226.
28. [6d] L. Micouin, T. Varea, C. Riche, A. Chiaroni, J.-C. Quirion, H.-P. Husson, Tetrahedron Lett. 1994, 35, 2529-2532.
29. [6e] M. J. Munchhof, A. I. Meyers, J. Am. Chem. Soc. 1995, 117, 5399-5400.
30. [6f] D. Francois, M. C. Lallemand, M. Selkti, A. Tomas, N. Kunesch, H.-P. Husson, Angew. Chem. Int. Ed. 1998, 37, 104-105.
31. [7a] C. Schneider, M. Rehfeuter, Synlett 1996, 212-214.
32. [7b] C. Schneider, M. Rehfeuter, Tetrahedron 1997, 53, 133-144;
33. for independent research in this area see: [7c] W. C. Black, A. Giroux, G. Greidanus, Tetrahedron Lett. 1996, 37, 4471-4474.
34. [7d] K. Tomooka, A. Nagasawa, S. Y. Wei, T. Nakai, Tetrahedron Lett. 1996, 37, 8899-8900.
35. [8a] C. Schneider, Synlett 1997, 815-817.
36. [8b] C. Schneider, A. Schuffenhauer, Eur. J. Org. Chem., in press.
37. [9a] C. Schneider, M. Rehfeuter, Tetrahedron Lett. 1998, 39, 9-12.
38. [9b] C. Schneider, M. Rehfeuter, Chem. Eur. J., 1999, 2850-2858.
39. C. Schneider, Eur. J. Org. Chem. 1998, 1661-1663.
40. C. Schneider, O. Reese, Angew. Chem., in preparation.
41. Preliminary communication: C. Schneider, C. Börner, Synlett 1998, 652-654.
42. F. Johnson, Chem. Rev. 1968, 68, 375-413.
43. J. L. Broeker, R. W. Hoffmann, K. N. Houk, J. Am. Chem. Soc. 1991, 113, 5006-5017.
44. F. Dumas, J. d'Angelo, Tetrahedron Lett. 1992, 33, 2005-2008.
45. Review: P. W. Hickmott, Tetrahedron 1982, 38, 1975-2050.
46. [17a] D. S. Grierson, M. Harris, H. P. Husson, J. Am. Chem. Soc. 1980, 102, 1064-1082.
47. [17b] D. S. Grierson, M. Harris, H. P. Husson, Tetrahedron 1983, 39, 3683-3694.
48. [17c] C. Caderas, R. Lett, L. E. Overman, M. H. Rabinowitz, L. A. Robinson, M. J. Sharp, J. Zablocki, J. Am. Chem. Soc. 1996, 118, 9073-9082.
49. R. K. Hill, T.-H. Chang, Tetrahedron 1965, 21, 2015-2019.
50. J. J. P. Stewart, J. Comput. Chem. 1989, 10, 109-123.