Transition metal-catalyzed intramolecular [4 + 2] cycloadditions: A novel method for the assembly of nitrogen heterocycles and its application to yohimban alkaloid synthesis

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 824-825

  Wender, Paul A ^a   Smith, Thomas E ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003267695     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9519827     Document Type: Article

References (31)

1. For the most recent work in this area see: (a) Wender, P. A.; Smith, T. E J. Org. Chem. 1995, 60, 2962. For the original work on intramolecular diene-diene and diene-alkyne cycloadditions, see: (b) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678 and (c) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6433-6434. For extensions to diene-alkene and diene-allene cycloadditions and other metal catalysts, see: (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. (e) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145 and references cited therein. For extensions to homologous vinylcyclopropane-alkyne systems see: (f) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
2. For the most recent work in this area see: (a) Wender, P. A.; Smith, T. E J. Org. Chem. 1995, 60, 2962. For the original work on intramolecular diene-diene and diene-alkyne cycloadditions, see: (b) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678 and (c) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6433-6434. For extensions to diene-alkene and diene-allene cycloadditions and other metal catalysts, see: (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. (e) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145 and references cited therein. For extensions to homologous vinylcyclopropane-alkyne systems see: (f) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
3. For the most recent work in this area see: (a) Wender, P. A.; Smith, T. E J. Org. Chem. 1995, 60, 2962. For the original work on intramolecular diene-diene and diene-alkyne cycloadditions, see: (b) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678 and (c) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6433-6434. For extensions to diene-alkene and diene-allene cycloadditions and other metal catalysts, see: (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. (e) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145 and references cited therein. For extensions to homologous vinylcyclopropane-alkyne systems see: (f) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
4. For the most recent work in this area see: (a) Wender, P. A.; Smith, T. E J. Org. Chem. 1995, 60, 2962. For the original work on intramolecular diene-diene and diene-alkyne cycloadditions, see: (b) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678 and (c) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6433-6434. For extensions to diene-alkene and diene-allene cycloadditions and other metal catalysts, see: (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. (e) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145 and references cited therein. For extensions to homologous vinylcyclopropane-alkyne systems see: (f) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
5. For the most recent work in this area see: (a) Wender, P. A.; Smith, T. E J. Org. Chem. 1995, 60, 2962. For the original work on intramolecular diene-diene and diene-alkyne cycloadditions, see: (b) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678 and (c) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6433-6434. For extensions to diene-alkene and diene-allene cycloadditions and other metal catalysts, see: (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. (e) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145 and references cited therein. For extensions to homologous vinylcyclopropane-alkyne systems see: (f) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
6. For the most recent work in this area see: (a) Wender, P. A.; Smith, T. E J. Org. Chem. 1995, 60, 2962. For the original work on intramolecular diene-diene and diene-alkyne cycloadditions, see: (b) Wender, P. A.; Ihle, N. C. J. Am. Chem. Soc. 1986, 108, 4678 and (c) Wender, P. A.; Jenkins, T. E. J. Am. Chem. Soc. 1989, 111, 6433-6434. For extensions to diene-alkene and diene-allene cycloadditions and other metal catalysts, see: (d) Wender, P. A.; Jenkins, T. E.; Suzuki, S. J. Am. Chem. Soc. 1995, 117, 1843-1844. (e) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145 and references cited therein. For extensions to homologous vinylcyclopropane-alkyne systems see: (f) Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721.
7. For a recent review of the intramolecular Diels-Alder reaction, see: Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 5, pp 513-550.
8. For Ni(0)-mediated cyclizations of diynes with nitrogen linkers see: (a) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546 and references therein. (b) Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140-3145. (c) Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570-8572.
9. For Ni(0)-mediated cyclizations of diynes with nitrogen linkers see: (a) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546 and references therein. (b) Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140-3145. (c) Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570-8572.
10. For Ni(0)-mediated cyclizations of diynes with nitrogen linkers see: (a) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539-546 and references therein. (b) Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 3140-3145. (c) Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. J. Am. Chem. Soc. 1988, 110, 8570-8572.
11. The Alkaloids; Manske, R. H. F., Ed ; Academic: New York, 1951-1994: Vols. 1-45.
12. For an excellent review see: Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer-Verlag: New York, 1992; Vol. 8, pp 197-319.
13. 3 in THF (Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D., Jr.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712).
14. 3 in THF (Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D., Jr.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712).
15. 3 in THF (Henry, J. R.; Marcin, L. R.; McIntosh, M. C.; Scola, P. M.; Harris, D., Jr.; Weinreb, S. M. Tetrahedron Lett. 1989, 30, 5709-5712).
16. 2O/hexanes) to give the tetrahydroisoindole 2 (55.2 mg, 91%) as a white powder. All new compounds were characterized by IR and NMR spectroscopy and provided satisfactory elemental or exact mass analyses.
17. The highly electron-withdrawing ligand tris(hexafluoroisopropyl) phosphite has an accelerating effect in these cycloadditions. For the electronic and steric parameters of this versatile ligand, see: Van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 37, 1973. For the best synthetic preparation, see: Sakatsume, O.; Yamane, H.; Takaku, H.; Yamamoto, N. Nucleic Acids Res. 1990, 18, 3327.
18. The highly electron-withdrawing ligand tris(hexafluoroisopropyl) phosphite has an accelerating effect in these cycloadditions. For the electronic and steric parameters of this versatile ligand, see: Van Leeuwen, P. W. N. M.; Roobeek, C. F. Tetrahedron 1981, 37, 1973. For the best synthetic preparation, see: Sakatsume, O.; Yamane, H.; Takaku, H.; Yamamoto, N. Nucleic Acids Res. 1990, 18, 3327.
19. For a mechanistic interpretation of the nickel-catalyzed reactions see refs 1a and 1c.
20. Following the protocol of: Hayakawa, K.; Takewaki, M.; Fujimoto, I.; Kanematsu, K. J. Org. Chem. 1986, 51, 5100-5105.
21. Martin, S. F.; Williamson, S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48, 5170
22. Negishi, E.-i.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336-3346.
23. Lounasmaa, M.; Karvinen, E.; Jokela, R. Tetrahedron 1987, 43, 2135-2146.
24. Fujikara, S.; Inoue, M.; Utimoto, K.; Nozaki, H. Tetrahedron Lett 1984, 25, 1999-2002.
25. (a) Aubé, J.; Ghosh, S.; Tanol, M. J. Am. Chem. Soc. 1994, 116, 9009-9018.
26. (b) Aubé, J.; Wang, Y.; Hammond, M.; Tanol, M.; Takusagawa, F.; Vander Velde, D. J. Am. Chem. Soc. 1990, 112, 4879-4891.
27. Naito, T.; Miyata, O.; Tada, Y.; Nishiguchi, Y., Kiguchi, T.; Ninomiya, I. Chem. Pharm. Bull. 1986, 34, 4144-4149
28. The products of the hydrogenation had spectra consistent with those from yohimban and alloyohimban: (a) Hua, D. H.; Bharathi, S. N.; Panagadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998-7007. (b) Reference 15b. (c) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645-3655.
29. The products of the hydrogenation had spectra consistent with those from yohimban and alloyohimban: (a) Hua, D. H.; Bharathi, S. N.; Panagadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998-7007. (b) Reference 15b. (c) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645-3655.
30. The products of the hydrogenation had spectra consistent with those from yohimban and alloyohimban: (a) Hua, D. H.; Bharathi, S. N.; Panagadan, J. A. K.; Tsujimoto, A. J. Org. Chem. 1991, 56, 6998-7007. (b) Reference 15b. (c) Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645-3655.
31. Naito, T.; Hirata, Y.; Miyata, O.; Ninomiya, I. J. Chem. Soc., Perkin Trans. 1 1988, 2219-2225 and references therein.