Conjugate addition of organocuprates to chiral bicyclic δ-lactams. Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines

Organic Letters

Volumn 3, Issue 4, 2001, Pages 611-614

  Amat, Mercedes ^a   Pérez, Maria ^a   Llor, Núria ^a   Bosch, Joan ^a   Lago, Elena ^b   Molins, Elies ^b  

^a UNIVERSITY OF BARCELONA   (Spain)

^b INSTITUT DE CIÈNCIA DE MATERIALS DE BARCELONA ICMAB CSIC   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; LACTAM; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

HETEROCYCLIC COMPOUNDS, 2-RING; LACTAMS; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM;

EID: 0035932039     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol007010p     Document Type: Article

References (48)

1. (a) Fodor G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W. Ed.; Wiley: New York, 1985; Vol. 3, Chapter 1, pp 1-90.
2. (b) Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1987; Vol. 5, Chapter 1, pp 1-54.
3. (c) Takahata, H.; Momose, T. In The Alkaloids: Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 44, Chapter 3, pp 189-256.
4. (d) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, 1996; Vol. 10, Chapter 2, pp 155-299.
5. For reviews, see: (a) Wang, C.-L. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 585.
6. (b) Angle, S. R.; Breitenbucher, J. G. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 16, pp 453-502.
7. (c) Leclercq, S.; Daloze, D.; Braekman, J.-C. Org. Prep. Proced. Int. 1996, 28, 501.
8. (d) Nadin, A. Contemp. Org. Synth. 1997, 4, 387.
9. (d) Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 633.
10. (a) Amat M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223.
11. (b) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7084.
12. (c) Munchhof, M. J.; Meyers, A. I. J. Org. Chem. 1995, 60, 7086.
13. Amat, M.; Pschenichnyi, G.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 3091.
14. Dwyer, M. P.; Lamar, J. E.; Meyers, A. I. Tetrahedron Lett. 1999, 40, 8965.
15. (a) Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399.
16. (b) Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977.
17. Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419.
18. Amat, M.; Bosch, J.; Hidalgo, J.; Cantó, M.; Pérez, M.; Llor, N.; Molins, E.; Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
19. For a review, see: Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1.
20. (a) Nagashima, H.; Ozaki, N.; Washiyama, M.; Itoh, K. Tetrahedron Lett. 1985, 26, 657.
21. (b) Hagen, T. Synlett 1990, 63.
22. (c)Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057.
23. (d) Woo, K.-C.; Jones, K. Tetrahedron Lett. 1991, 32, 6949.
24. (e) Herdeis, C.; Hubmann, H. P. Tetrahedron: Asymmetry 1992, 3, 1213.
25. (f) Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1992, 33, 7969.
26. (g) Hashimoto, M.; Hashimoto, K.; Shirahama, H. Tetrahedron 1996, 32, 1931.
27. (h) Diaz, A.; Siro, J. G.; García-Navío, J. L.; Vaquero, J. J.; Alvarez-Builla, J. Synthesis 1997, 559.
28. (i) Baussanne, I.; Royer, J. Tetrahedron Lett. 1998, 39, 845.
29. (j) Luker, T.; Koot, W.-J.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1998, 63, 220.
30. (k) Cossy, J.; Cases, M.; Gomez-Pardo, D. Synlett 1998, 507.
31. (a) Hanessian, S.; Ratovelomanana, V. Synlett 1990, 501.
32. (b) Baldwin, J. E.; Moloney, M. G.; Shim, S. B. Tetrahedron Lett. 1991, 32, 1379.
33. (c) Meyers, A. I.; Snyder, L. J. Org. Chem. 1992, 57, 3814.
34. (d) Meyers, A. I.; Snyder, L. J. Org. Chem. 1993, 58, 36.
35. (e) Goswami, R.; Moloney, M. G. Chem. Commun. 1999, 2333.
36. (a) Takano, S.; Sato, M.; Ogasawara, K. Heterocycles 1981, 16, 799.
37. (b) Fujii, T.; Ohba, M.; Akiyama, S. Chem. Pharm. Bull. 1985, 33, 5316.
38. (c) Fujii, T.; Ohba, M.; Sakaguchi, J. Chem. Pharm. Bull. 1987, 35, 3628.
39. (a) Herdeis, C.; Kaschinski, C.; Karla, R.; Lotter, H. Tetrahedron: Asymmetry 1996, 7, 867. See also:
40. (b) Fleming, I.; Reddy, N. L.; Takaki, K.; Ware, A. C. J. Chem. Soc., Chem. Commun. 1987, 1472.
41. The same trans relative stereochemistry is obtained in the conjugate addition to γ-substituted α,β-unsaturated δ-lactones: Yoda, H.; Naito, S.; Takabe, K.; Tanaka, N.; Hosoya, K. Tetrahedron Lett. 1990, 31, 7623. See also refs 10g and 13b.
42. Amat, M.; Llor, N.; Hidalgo, J.; Bosch, J. Tetrahedron: Asymmetry 1997, 8, 2237.
43. 13C NMR), analytical, and/or HRMS data were obtained for all new compounds.
44. For examples in the racemic series, see: (a) McErlane, K. M. J.; Casy, A. F. Can. J. Chem. 1972, 50, 2149.
45. (b) Pridgen, L. N. J. Org. Chem. 1974, 39, 3059.
46. (c) Gless, R. D., Rapoport, H. J. Org. Chem. 1979, 44, 1324.
47. Kozikowski, A. P.; Araldi, G. L.; Boja, J.; Meil, W. M.; Johnson, K. M.; Flippen-Anderson, J. L.; George, C.; Saiah, E. J. Med. Chem. 1998, 41, 1962.
48. -3.