Novel Pd(0)-catalyzed intramolecular reactions of allylic acetates with allenic moieties followed by tandem cyclization

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2602-2603

  Doi, Takayuki ^a   Yanagisawa, Arata ^a   Nakanishi, Sadahiro ^a   Yamamoto, Keiji ^a   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000810091     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960385x     Document Type: Article

References (38)

1. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer Verlag: New York, 1980. Trost, B. M. Acc. Chem Res. 1980, 13, 385. Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Semmelhaek, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 585-661.
2. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer Verlag: New York, 1980. Trost, B. M. Acc. Chem Res. 1980, 13, 385. Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Semmelhaek, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 585-661.
3. Tsuji, J. Organic Synthesis with Palladium Compounds; Springer Verlag: New York, 1980. Trost, B. M. Acc. Chem Res. 1980, 13, 385. Godleski, S. A. Nucleophiles with Allyl-Metal Complexes. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, L, Semmelhaek, M. F., Eds.; Pergamon Press: New York, 1991; Vol. 4, pp 585-661.
4. Oppolzer, W.; Gaudin, J.-M. Helv. Chim. Acta 1987, 70, 1477. Oppolzer, W. In Organometallic Reagents in Organic Synthesis; Bateson, J. H., Mitchell, M. B., Eds.; Academic Press: London, 1994, p 161. For a review, see: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 46-61.
5. Oppolzer, W.; Gaudin, J.-M. Helv. Chim. Acta 1987, 70, 1477. Oppolzer, W. In Organometallic Reagents in Organic Synthesis; Bateson, J. H., Mitchell, M. B., Eds.; Academic Press: London, 1994, p 161. For a review, see: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 46-61.
6. Oppolzer, W.; Gaudin, J.-M. Helv. Chim. Acta 1987, 70, 1477. Oppolzer, W. In Organometallic Reagents in Organic Synthesis; Bateson, J. H., Mitchell, M. B., Eds.; Academic Press: London, 1994, p 161. For a review, see: Oppolzer, W. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, pp 46-61.
7. Yamamoto, K.; Terakado, M.; Murai, K.; Miyazawa, M.; Tsuji, J.; Takahashi, K.; Mikami, K. Chem. Lett. 1989, 955. Terakado, M.; Murai, K.; Miyazawa, M.; Yamamoto, K. Tetrahedron 1994, 50, 5705.
8. Yamamoto, K.; Terakado, M.; Murai, K.; Miyazawa, M.; Tsuji, J.; Takahashi, K.; Mikami, K. Chem. Lett. 1989, 955. Terakado, M.; Murai, K.; Miyazawa, M.; Yamamoto, K. Tetrahedron 1994, 50, 5705.
9. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Heck, R. F. Acc. Chem. Res. 1979, 12, 146; Org. React. 1982, 27, 345.
10. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Heck, R. F. Acc. Chem. Res. 1979, 12, 146; Org. React. 1982, 27, 345.
11. de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379. Heck, R. F. Acc. Chem. Res. 1979, 12, 146; Org. React. 1982, 27, 345.
12. For an excellent example of stereocontroled tandem eyclization using Pd(0)-catalyzed olefin allylation followed by Heck reaction, see: Oppolzer, W.; DeVita, R. J. J. Org. Chem. 1991, 56, 6256.
13. For tandem cyclization anion capture, see: Grigg, R.; Sukirthalingam, S.; Sridharan, V. Tetrahedron Lett. 1991, 32, 2545. Grigg, R.; Sridharan, V.; Sukirthalingam, S. Ibid. 1991, 32, 3855.
14. For tandem cyclization anion capture, see: Grigg, R.; Sukirthalingam, S.; Sridharan, V. Tetrahedron Lett. 1991, 32, 2545. Grigg, R.; Sridharan, V.; Sukirthalingam, S. Ibid. 1991, 32, 3855.
15. Keese, R.; Guidetti-Grept, R.; Herzog, B. Tetrahedron Lett. 1992, 33, 1207.
16. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
17. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
18. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
19. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
20. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
21. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
22. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
23. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
24. For intermolecular carbopalladation of allenes, see: (a) Stevens, R. R ; Shier, G. J. Organomet. Chem 1970, 21, 495. (b) Shimizu, I.; Tsuji J. Chem. Lett. 1984, 233. (c) Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274. (d) Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun. 1984, 905. (e) Ahmar, M.; Barieux, J.-J.; Cazes, B.; Gore, J. Tetrahedron 1987, 43, 513. (f) Yamamoto, Y.; Al-Masum, M.; Asao, N. J. Am. Chem. Soc. 1994, 116, 6019. (g) Trost, B. M.; Gerusz, V. J. J. Am. Chem. Soc. 1995, 117, 5156. For intramolecular version, see: (h) Ma, S.; Negishi, E. J. Org. Chem 1994 59, 4730. (i) Ma. S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
25. Only stoichiometric reactions of the π-allylpalladium complex with allenes are known; see: Hughes, R. P.; Powell, J. J. Organomet. Chem. 1969, 20, P17; 1973, 60, 409.
26. Only stoichiometric reactions of the π-allylpalladium complex with allenes are known; see: Hughes, R. P.; Powell, J. J. Organomet. Chem. 1969, 20, P17; 1973, 60, 409.
27. Mikami, K; Shimizu, M. Chem. Rev. 1992, 92, 1021.
28. Schoenberg, A.; Bartoletti, I.; Heck, R. F. J. Org. Chem. 1974, 39, 3318.
29. 8f carbopalladation to an allene with this particular regioselection had been reported. However, it was reasonably postulated as the hydropalladation mechanism with usual regioselection in ref 8g.
30. For amino- and alkoxypalladation to allenes to generate α-vinylpalladium intermediates, see: Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun 1984, 905. Hegedus, L. S.; Kambe, N., Tamaru, R.; Woodgate, P. D. Organometallics 1983, 2, 1658. Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009.
31. For amino- and alkoxypalladation to allenes to generate α-vinylpalladium intermediates, see: Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun 1984, 905. Hegedus, L. S.; Kambe, N., Tamaru, R.; Woodgate, P. D. Organometallics 1983, 2, 1658. Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009.
32. For amino- and alkoxypalladation to allenes to generate α-vinylpalladium intermediates, see: Alper, H.; Hartstock, F. W.; Despeyroux, B. J. Chem. Soc., Chem. Commun 1984, 905. Hegedus, L. S.; Kambe, N., Tamaru, R.; Woodgate, P. D. Organometallics 1983, 2, 1658. Lathbury, D.; Vernon, P.; Gallagher, T. Tetrahedron Lett. 1986, 27, 6009.
33. Intraannluar diastereoselction of the Pd(0)-catalyzed cyclization of acyclic compounds is more or less trans dominant, whereas that of the Ni(0)-catalyzed cyclization is known to be exclusively cis: Oppolzer, W.; Keller, T. H.; Bedoya-Zurita, M.; Stone, C. Tetrahedron Lett. 1989, 30, 5883. See also refs 2 and 3.
34. The low yields in the Pd(0)-catalyzed cyclization of allenes are due to the dimerization of allenes; see: Shier, G. D. J Organomet. Chem. 1967, 10, P15. Coulson, D. R. J Org. Chem. 1973, 38, 1483.
35. The low yields in the Pd(0)-catalyzed cyclization of allenes are due to the dimerization of allenes; see: Shier, G. D. J Organomet. Chem. 1967, 10, P15. Coulson, D. R. J Org. Chem. 1973, 38, 1483.
36. The reaction did not proceed under argon. The presence of carbon monoxide could accelerate the reductive elimination of the intermediate 14 See: Murahashi, S.-I.; Imada, Y.; Taniguchi, Y.; Higashiura, S. J. Org Chem. 1933, 58, 1538. Yamamoto, T.; Akimoto, M. Yamamoto, A. Organometallics 1986, 5, 1559.
37. The reaction did not proceed under argon. The presence of carbon monoxide could accelerate the reductive elimination of the intermediate 14 See: Murahashi, S.-I.; Imada, Y.; Taniguchi, Y.; Higashiura, S. J. Org Chem. 1933, 58, 1538. Yamamoto, T.; Akimoto, M. Yamamoto, A. Organometallics 1986, 5, 1559.
38. The bicyclic products were also produced in 18% yield via β-hydride elimination of the intermediates such as 18.