Stereoselective Synthesis of 2,5,6-Trisubstituted Piperidines

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2029-2031

  Harris, Joel M ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

OXIDATION-REDUCTION; PIPERIDINES;

EID: 0037071940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025859v     Document Type: Article

References (50)

1. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988. Elbein, A. D.; Molyneux, R. In Alkaloids, Chemical and Biological Perspectives; Pelletier, W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1. Gogfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321.
2. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988. Elbein, A. D.; Molyneux, R. In Alkaloids, Chemical and Biological Perspectives; Pelletier, W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1. Gogfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321.
3. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988. Elbein, A. D.; Molyneux, R. In Alkaloids, Chemical and Biological Perspectives; Pelletier, W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1. Gogfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321.
4. Bosch, J.; Bonjoch, J. Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elsevier: New York, 1988; Vol. 1, p 31. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 6, 633.
5. Bosch, J.; Bonjoch, J. Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elsevier: New York, 1988; Vol. 1, p 31. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 6, 633.
6. Bosch, J.; Bonjoch, J. Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elsevier: New York, 1988; Vol. 1, p 31. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 6, 633.
7. For recent reviews, see: Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825. Lekevits, E. Chem. Heterocycl. Compd. 1995, 31, 639.
8. For recent reviews, see: Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825. Lekevits, E. Chem. Heterocycl. Compd. 1995, 31, 639.
9. For representative examples, see: Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
10. For representative examples, see: Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
11. For representative examples, see: Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
12. For representative examples, see: Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
13. For representative examples, see: Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
14. For representative examples, see: Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
15. Comins, D. L.; Killpack, M. O. J. Am. Chem. Soc. 1992, 114, 10973. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
16. Comins, D. L.; Killpack, M. O. J. Am. Chem. Soc. 1992, 114, 10973. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
17. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
18. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
19. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
20. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
21. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
22. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
23. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
24. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew Chem., Int. Ed. 1998, 37, 104.
25. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew Chem., Int. Ed. 1998, 37, 104.
26. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew Chem., Int. Ed. 1998, 37, 104.
27. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H.-P. Angew Chem., Int. Ed. 1998, 37, 104.
28. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; Vol. 55, pp 91-258. Michael, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, pp 185-288.
29. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; Vol. 55, pp 91-258. Michael, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, pp 185-288.
30. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; Vol. 55, pp 91-258. Michael, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, pp 185-288.
31. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 2001; Vol. 55, pp 91-258. Michael, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1993; Vol. 43, pp 185-288.
32. For an excellent review of the subject, see: Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimizu, T.; Swaminathan, S.; Xi, N. Synlett 1998, 105.
33. Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2001, 3, 401.
34. Zhou, W. S.; Lu, Z. H.; Xu, Y. M.; Liao, L. X.; Wang, Z. M. Tetrahedron 1999, 55, 11959. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. Altenbach, H. J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983.
35. Zhou, W. S.; Lu, Z. H.; Xu, Y. M.; Liao, L. X.; Wang, Z. M. Tetrahedron 1999, 55, 11959. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. Altenbach, H. J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983.
36. Zhou, W. S.; Lu, Z. H.; Xu, Y. M.; Liao, L. X.; Wang, Z. M. Tetrahedron 1999, 55, 11959. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. J. Chem. Soc., Perkin Trans. 1 1995, 2599. Altenbach, H. J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983.
37. Lu, Z. H.; Zhou, W. S. J. Chem. Soc., Perkin Trans. 1 1993, 593. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. Tetrahedron Lett. 1995, 36, 1291.
38. Lu, Z. H.; Zhou, W. S. J. Chem. Soc., Perkin Trans. 1 1993, 593. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. Tetrahedron Lett. 1995, 36, 1291.
39. For some related additions, see: Koulocheri, S. D.; Magiatis, P.; Skaltsounis, A. L.; Hartoutounian, S. A. Tetrahedron 2000, 56, 6135.
40. The 2-axial conformation of N-acylpiperidines is well established. See: Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
41. For some recent results in this area, see: Liao, L. X.; Wang, Z. M.; Zhang, Z. X.; Zhou, W. S. Tetrahedron: Asymmetry 1999, 10, 3649.
42. Apostolopoulos, C. D.; Couladouros, E. A.; Georgiadis, M. P. Liebigs Ann. Chem. 1994, 781. Couladouros, E. A.; Apostolopoulos, C. D.; Georgiadis, M. P. Carbohydr. Res. 1993, 249, 399.
43. Apostolopoulos, C. D.; Couladouros, E. A.; Georgiadis, M. P. Liebigs Ann. Chem. 1994, 781. Couladouros, E. A.; Apostolopoulos, C. D.; Georgiadis, M. P. Carbohydr. Res. 1993, 249, 399.
44. Shono, T.; Matsumara, Y.; Tsubata, K.; Uchida, K. J. Org. Chem. 1986, 51, 2590.
45. Hopman, J. C. P.; van de Berg, E.; Ollero, L. O.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315.
46. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
47. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
48. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
49. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
50. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.