Asymmetric dipolar cycloaddition reactions: A practical, convergent synthesis of chiral pyrrolidines

Tetrahedron Asymmetry

Volumn 8, Issue 6, 1997, Pages 883-887

  Ma, Zhenkun ^a   Wang, Sanyi ^a   Cooper, Curt S ^a   Fung, Anthony K L ^a   Lynch, John K ^a   Plagge, Frederick ^a   Chu, Daniel T W ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030909024     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00049-9     Document Type: Article

References (31)

1. (a) Chu, D. T. W.; Li, Q.; Claiborne, A.; Raye-Passarelli, K.; Cooper, C.; Fung, A.; Lee, C; Tanaka, S. K.; Shen, L.; Donner, R; Armiger, Y. L.; Plattner, J. J. in 34th ICCAC Abstract, 1994, Abstract F41.
2. (b) Flamm, R. K.; Vojtko, C.; Chu, D. T.; Li, Q.; Beyer, J.; Hensey, D.; Ramer, N.; Clement, J. J.; Tanaka, S. K. Antimicrob. Agents Chemotherap. 1995, 39, 964-970.
3. Shen, L. L.; Mitscher, L. A.; Sharma, P. N.; O'Donnell, T. J.; Chu, D. W. T.; Cooper, C. S.; Rosen, T.; Pernet, A. G. Biochemistry 1989, 28, 3886-3894.
4. For a recent review on enantioselective synthesis of pyrrolidines see: Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221-3235.
5. (a) Terao, Y.; Kotaki, H.; Imai, N.; Achiwa, K. Chem. Pharm. Bull., Jpn. 1985, 33, 2762-2766.
6. (b) Laborde, E. Tetrahedron Lett. 1992, 33, 6607-6610.
7. (c) Begue, J.-P; Bonnet-Delpon, D.; Lequeux, T. Tetrahedron Lett. 1993, 34, 3279-3282.
8. (d) Nyerges, M.; Balazs, L.; Kadas, I.; Bitter, I.; Kovesdi, I.; Toke, L. Tetrahedron 1995, 51. 6783-6788.
9. For some applications of this useful reaction see: (a) Williams, R. M.; Fegley, G. J. Tetrahedron Lett. 1992, 33, 6755-6758.
10. (b) Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J Org. Chem. 1994, 59, 6510-6511.
11. (c) Garner, P.; Ho, W. B. J. Org. Chem. 1990, 55, 3973-3975.
12. (d) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1990, 1239-1242.
13. For asymmetric 1,3-dipolar cycloaddition involving azomethine ylides see: (a) Waldmann, H.; Blaser, E.; Jansen, M.; Letschert, H.-P. Angew. Chem. Int. Ed. Engl. 1994, 33, 683-685.
14. (b) Peyronel, J.-F.; Grisoni, S.; Carboni, B.; Courgeon, T.; Carrie, R. Tetrahedron 1994, 50, 189-198.
15. (c) Patzel, M.; Galley, G.; Johns, P. G.; Chrapkowsky, A. Tetrahedron Lett. 1993, 34, 5707-5710.
16. (d) Williams, R. M.; Zhai, W; Aldous, D. J.; Aldous, S. C. J. Org. Chem. 1992, 57, 6527-6532.
17. (e) Fray, A.; Meyers, A. I. Tetrahedron Lett. 1992, 33, 3575-3578.
18. (f) Harwood, L. M.; Macro, J.; Watkin, D.; Williams, C. E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127-1130.
19. (g) Anslow, A. S.; Harwood, L. M.; Philips, H.; Watkin, D.; Wong, L. H. Tetrahedron: Asymmetry 1991, 2, 1343-1358.
20. (h) Coulter. T.; Grigg, R.; Malone, J. E; Sridharan, V. Tetrahedron Lett. 1991, 32, 5417-5420.
21. (i) Kanemasa, S.; Hayashi, T.; Tanaka, J.; Yamomoto, H.; Sakurai, T. J. Org. Chem. 1991, 56, 4473-4481.
22. (j) Deprez, P.; Royer, J.; Husson, H.-P. Tetrahedron: Asymmetry 1991, 2, 1189-1192.
23. (k) Kanemasa, S.; Yamamoto, H. Tetrahedron Lett. 1990, 31, 3633-3636.
24. (l) Wee, A. G. H. J Chem. Soc. Perkin Trans. I 1989, 1363-1364.
25. (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238-1256.
26. (b) Evans, D. A.; Lectka, T; Miller, S. J. Tetrahedron Lett. 1993, 34, 7027-7030.
27. (c) Evans, D, A.; Miller, S. J.; Lectka, T.J. Am. Chem. Soc. 1993, 115, 6460-6461.
28. We thank Mr. Rodger Henry for performing X-ray crystallography analysis.
29. Ninomiya, K.; Shioiri, T; Yamada, S. Tetrahedron 1974, 30, 2151.
30. Adger, B. M.; O'Farrell, C.; Lewis, N. J.; Mitchell, M. B. Synthesis 1987, 53.
31. Smith, L. I.; Rogier, E. R. J. Am. Chem. Soc. 1951, 73, 3831.