Asymmetric syntheses of 2-substituted and 2,5-disubstituted pyrrolidines from (3S,5R,7aR)-5-(benzotriazol-1-yl)-3-phenyl[2,1-b]oxazolopyrrolidine

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1979-1985

  Katritzky, Alan R ^a   Cui, Xi Lin ^a   Yang, Baozhen ^a   Steel, Peter J ^b  

^a University of Florida ^*  (United States)

^b UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

5 (BENZOTRIAZOL 1 YL) 3 PHENYL[2,1 B]OXAZOLOPYRROLIDINE; BENZOTRIAZOLE DERIVATIVE; GLYCINE DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PYRROLIDINE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; TRIMETHYLSILYL DERIVATIVE; UNCLASSIFIED DRUG; ZINC COMPLEX;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOLECULAR MODEL; REACTION ANALYSIS; STRUCTURE ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0033583019     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9821426     Document Type: Article

References (62)

1. (a) Braekman, J. C.; Daloze, D. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1990; Vol. 6, p 421.
2. (b) Tufariello, J. J. Acc. Chem. Res. 1979, 12, 396.
3. (c) Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927.
4. (a) Elbein, A.; Molyneux, R. I. In Alkaloids, Chemical and Biological Perspectives; Pelletier, S. W., Ed.; John Wiley: New York, 1990; Vol. 5, p 1-54.
5. (b) Attygalle, A. B.; Morgan, E. D. Chem. Soc. Rev. 1984, 13, 245.
6. (c) Schmeltz, I.; Hoffmann, D. Chem. Rev. 1977, 77, 295.
7. (a) Elliott, R. L.; Kopecka, H.; Lin, N.-H.; He, Y.; Garvey, D. S. Synthesis 1995, 772.
8. (b) Lin, N.-H.; Carrera, G. M., Jr.; Anderson, D. J. J. Med. Chem. 1994, 37, 3542.
9. (a) Huryn, D. M. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, p 64.
10. (b) Yamamoto, Y.; Hoshino, J.; Fujimoto, Y.; Ohmoto, J.; Sawada, S. Synthesis 1993, 298.
11. (c) Koh, K.; Ben, R. N.; Durst, T. Tetrahedron Lett. 1994, 35, 375.
12. (d) Corey, E. J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990, 55, 784.
13. (e) DeNinno, M. P.; Perner, R. J.; Lijewski, L. Tetrahedron Lett. 1990, 31, 7415.
14. (f) Jones, T. K.; Mohan, J. J.; Xavier, L. C.; Blacklock, T. J.; Mathre, D. J.; Sohar, P.; Jones, E. T. T.; Reamer, R. A.; Roberts, F. E.; Grabowski, E. J. J. J. Org. Chem. 1991, 56, 763.
15. For some recent examples, see: Racemic synthesis: (a) Jones, T. H.; Franko, J. B.; Blum, M. S.; Fales, H. M. Tetrahedron Lett. 1980, 21, 789.
16. (b) Jones,T. H.; Highet, R. J.; Don, A. W.; Blum, M. S. J. Org. Chem. 1986, 51, 2712.
17. (c) Chastanet, J.; Roussi, G. J. Org. Chem. 1988, 53, 3808.
18. (d) Wittland, C.; Arend, M.; Risch, N. Synthesis 1996, 367.
19. (e) Backvall, J.-E.; Schink, H. E.; Renko, Z. D. J. Org. Chem. 1990, 55, 826.
20. (f) Cancho, Y.; Martin, J. M.; Martinez, M.; Liebaria, A.; Moreto, J. M.; Delgado, A. Tetrahedron 1998, 54, 1221.
21. Optically active synthesis: (g) Shiosaki, K.; Rapoport, H. J. Org. Chem. 1985, 50, 1229.
22. (h) Machinaga, N.; Kibayashi, C. J. Org. Chem. 1991, 56, 1386.
23. (i) Meyers, A. I.; Burgess, L. E. J. Org. Chem. 1991, 56, 2294.
24. (j) Lorthiois, E.; Marek, I.; Normant, J. F. J. Org. Chem. 1998, 63, 2442.
25. (k) Enierga, G.; Hockless, D. C. R.; Perlmutter, P.; Rose, M.; Sjoberg, S.; Wong, K. Tetrahedron Lett. 1998, 39, 2813.
26. (l) Sasaki, N. A.; Sagnard, I. Tetrahedron 1994, 50, 7093.
27. (m) Dockner, M.; Sasaki, N. A.; Potier, P. Heterocycles 1996, 42, 529.
28. For some examples, see the following. Racemic synthesis: (a) Fraser, R. R.; Passannanti, S. Synthesis 1976, 540.
29. (b) Jones, T. H.; Blum, M. S.; Fales, H. M. Tetrahedron 1982, 38, 1949.
30. (c) Gessner, W.; Takahashi, K.; Brossi, A.; Kowalski, M.; Kaliner, M. A. Helv. Chim. Acta 1987, 70, 2003.
31. Optically active synthesis: (d) Saliou, C.; Fleurant, A.; Celerier, J. P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365.
32. (e) Haviari, G.; Celerier, J. P.; Petit, H.; Lhommet, G.; Gardette, D.; Gramain, J. C. Tetrahedron Lett. 1992, 33, 4311.
33. (f) Viso, A.; Lee, N. E.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 9373.
34. (g) Chan, P. W. H.; Cottrell, I. F.; Moloney, M. G. Tetrahedron Lett. 1997, 38, 5891.
35. (h) Bardou, A.; Celerier, J. P.; Lhommet, G. Tetrahedron Lett. 1997, 38, 8507.
36. (i) Blot, J.; Bardou, A.; Bellec, C.; Fargeau-Bellassoued, M.-C.; Celerier, J. P.; Lhommet, G.; Gardette, D.; Gramain, J.-C. Tetrahedron Lett. 1997, 38, 8511.
37. (j) Sudau, A.; Nubbemeyer, U. Angew. Chem., Int. Ed. 1998, 37, 1140.
38. Stevens, R. V. Acc. Chem. Res. 1977, 70, 193.
39. (a) Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754.
40. (b) Bonin, M.; Grierson, D S.; Royer, J.; Husson, H.-P. Org. Synth. 1992, 70, 54.
41. (a) Huang, P.-Q.; Arseniyadis, S.; Husson, H.-P. Tetrahedron Lett. 1987, 28, 547.
42. (b) Royer, J.; Husson, H.-P. Tetrahedron Lett. 1987, 28, 6175.
43. (c) Arseniyadis, S.; Huang, P.-Q.; Husson, H.-P. Tetrahedron Lett. 1988, 29, 631.
44. (d) Arseniyadis, S.; Huang, P.-Q.; Piveteau, D.; Husson, H.-P. Tetrahedron 1988, 44, 2457.
45. Gauthier, I.; Royer, J.; Husson, H.-P. J. Org. Chem. 1997, 62, 6704.
46. (a) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1992, 57, 1059.
47. (b) Luker, T.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220.
48. (a) Baussanne, I.; Royer, J. Tetrahedron Lett. 1998, 39, 845.
49. (b) Baussanne, I. ; Travers, C. ; Royer, J. Tetrahedron Asymmetry 1998, 9, 797.
50. Katritzky, A. R.; Lan, X.; Yang, Z. J.; Denisko, O. V. Chem. Rev. 1998, 98, 409.
51. Shankar, B. B.; Kirkup, M. P.; McCombie, S. W.; Ganguly, A. K. Tetrahedron Lett. 1993, 34, 7171.
52. Katritzky, A. R.; Qiu, G.; Yang, B.; Steel, P. J. J. Org. Chem. 1998, 63, 6699.
53. Katritzky, A. R.; Cui, X.-L.; Yang, B.; Steel, P. J. Tetrahedron Lett. 1998, 39, 1697.
54. Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083.
55. Meyers, A. I.; Edwards, P. D.; Rieker, W. F.; Bailey, T. R. J. Am. Chem. Soc. 1984, 106, 3270.
56. (a) Roessler, F.; Ganzinger, D.; Johne, S.; Schopp, E.; Hesse, M. Helv. Chim. Acta 1978, 61, 1200.
57. (b) Langenskiold, T.; Lounasmaa, M. Heterocycles 1983, 20, 671.
58. For recent asymmetric syntheses see: (a) Smith, A. B., III; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1995, 117, 10879.
59. (b) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687.
60. (c) Maury, C.; Wang, Q.; Gharbaoui, T.; Chiadmi, M.; Tomas, A.; Royer, J.; Husson, H.-P. Tetrahedron 1997, 53, 3627.
61. Bhattacharya, A. K.; Thyagarajan, G. Chem. Rev. 1981, 81, 415.
62. Katritzky, A. R.; Bao, W.; Qi, M.; Fali, C. N.; Prakash, I. Tetrahedron Lett. 1998, in press.