Synthesis of substituted piperidines, indolizidines, quinolizidines, and pyrrolizidines via a cycloaddition strategy using acetylenic sulfones as alkene dipole equivalents

Organic Letters

Volumn 1, Issue 2, 1999, Pages 261-263

  Back, Thomas G ^a   Nakajima, Katsumasa ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001405570     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990592u     Document Type: Article

References (49)

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2. (b) Tanaka, K.; Kaji, A. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; Chapter 15.
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9. See ref 1a, Chapter 9, and Grossert, J. S. In The Chemistry of Sulphones and Sulphoxides; Patai, S., Rappoport, Z., Stirling, C. J. M., Eds.; Wiley: Chichester, 1988; Chapter 20.
10. For other examples of conjugate additions of nitrogen nucleophiles to acetylenic sulfones, see: (a) Back, T. G.; Bethell, R. J.; Parvez, M.; Wehrli, D. J. Org. Chem. 1998, 63, 7908.
11. (b) Truce, W. E.; Brady, D. G. J. Org. Chem. 1966, 31, 3543.
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19. An intramolecular acylation reaction of an enamine sulfone derived from a primary amine was recently exploited in the synthesis of pumiliotoxin C: Back, T. G.; Nakajima, K. J. Org. Chem. 1998, 63, 6566. To our knowledge, no cyclizations of enamine sulfones derived from cyclic amines have been reported, as are required for the introduction of nitrogen at a ring-fusion site in products 4.
20. For lead references, see the following. Piperidine alkaloids: (a) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1985; Vol. 26, pp 89-183.
21. (b) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol. 3, pp 1-90. Indolizidine and quinolizidine alkaloids:
22. (c) Howard, A. S.; Michael, J. P. In The Alkaloids: Brossi, A., Ed.; Academic Press: Orlando, 1986; Vol. 28, pp 183-308.
23. (d) Herbert, R. B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol. 3, pp 241-274. Pyrrolizidine alkaloids:
24. (e) Wróbel, J. T. In The Alkaloids; Brossi, A., Ed.; Academic Press: Orlando, 1985; Vol. 26, pp 327-384. For a list of other reviews of these classes of alkaloids, see:
25. (f) Dewick, P. M. Medicinal Natural Products; Wiley: Chichester, 1997; pp 371-374.
26. The chloroamines were prepared by the following procedures, (a) 5: Dolfini, J. E.; Dolfini, D. M. Tetrahedron Lett. 1964, 2103.
27. (b) 9: Piper, J. R.; Johnston, T. P. J. Org. Chem. 1963, 28, 981.
28. (c) For a similar procedure leading to racemic 11 from the corresponding racemic amino alcohol, see: Neth. Appl. Patent 6,600,184; July, 13, 1966; Chem. Abstr. 1967, 66, 2580r.
29. (c) For a similar procedure leading to racemic 11 from the corresponding racemic amino alcohol, see: Neth. Appl. Patent 6,600,184; July, 13, 1966; Chem. Abstr. 1967, 66, 2580r.
30. (d) 14 and 16: Norton, T. R.; Seibert, R. A.; Benson, A. A.; Bergstrom, F. W. J. Am. Chem. Soc. 1946, 68, 1572.
31. (e) Chloroamine 7 was prepared from methyl (S)3-(N-benzoylamino)butanoate by reduction with lithium aluminum hydride and chlorination with thionyl chloride.
32. For lead references, see: March, J. In Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992; pp 1083-1085.
33. The following acetylenic sulfones were prepared by literature methods. For 1a, see: (a) Chen, Z.; Trudell, M. L. Synth. Commun. 1994, 24, 3149.
34. (b) Back, T. G.; Collins, S.; Kerr, R. G. J. Org. Chem. 1983, 48, 3077. For 1b: see ref 5. For 1c, see ref 9b and
35. (c) Back, T. G.; Krishna, M. V. J. Org. Chem. 1987, 52, 4265. For 1d, see ref 9b. For 1f see:
36. (d) Back, T. G.; Lai, E. K. Y.; Muralidharan, K. R. J. Org. Chem. 1990, 55, 4595. Compound 1e was prepared via the general method of ref 9b, from the selenosulfonation of 3-butyn-1-ol, followed by protection as the tert-butyldimethylsilyl ether and selenoxide elimination.
37. 3).
38. In general, a small excess (10-20%) of the chloroamine hydrochloride was employed to compensate for possible losses during the liberation of the corresponding free base, which was generally used immediately and without purification. The yields in Table 1 were thus calculated on the basis of the acetylenic sulfone. When the preparation of 12 was repeated with equimolar amounts of the hydrochloride of 11 and 1b, the yield of 12 was 84%.
39. Product 22 is a dendrobatid alkaloid found in the toxic skin secretions of certain species of neotropical frogs. For a general review of these compounds, see: Daly, J. F.; Spande, T. F. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1986; Vol. 4, pp 1-274.
40. For previous syntheses of (-)-indolizidine 167B, see: (a) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151.
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42. (c) Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445.
43. (d) Fleurant, A.; Saliou, C.; Célérier, J. P.; Platzer, N.; Moc, T. V.; Lhommet, G. J. Heterocycl. Chem. 1995, 32, 255.
44. (e) Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 14, 3119.
45. (f) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513.
46. (g) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688.
47. 2).
48. 3-CN-TFA, see: Comins, D. L.; Weglarz, M. A. J. Org. Chem. 1991, 56, 2506.
49. 3, see: Marshall, J. A.; Cleary, D. G. J. Org. Chem. 1986, 51, 858.