Palladium-catalyzed carbonylation of homoallylic amine derivatives in the presence of a copper co-catalyst

Bulletin of the Chemical Society of Japan

Volumn 76, Issue 6, 2003, Pages 1251-1256

  Mizutani, Takanori ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBONYLATION; CATALYSIS; COPPER; DERIVATIVES; PALLADIUM; SALTS;

MONOCARBONYLATION;

AMINES;

2 PYRROLIDONE DERIVATIVE; 3 METHYL 2 PYRROLIDONE DERIVATIVE; AMINE; COPPER; COPPER CHLORIDE; GAMMA LACTAM DERIVATIVE; N TOSYLHOMOALLYLAMINE; PALLADIUM; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038052647     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.76.1251     Document Type: Article

References (34)

1. H. M. Colquhoun, D. J. Thompson, and M. V. Twigg, "Carbonylation," Plenum Press, New York (1991).
2. J. Falbe and F. Korte, Chem. Ber., 98, 1928 (1965).
3. J. F. Knifton, J. Organomet. Chem., 188, 223 (1980).
4. I. Ojima, A. Korda, and W. R. Shay, J. Org. Chem., 56, 2024 (1991).
5. B. E. Ali, K. Okuro, G. Vasapollo, and H. Alper, J. Am. Chem. Soc., 118, 4264 (1996); K. Okuro, H. Kai, and H. Alper, Tetrahedron.-Asymmetry, 8, 2307 (1997).
6. B. E. Ali, K. Okuro, G. Vasapollo, and H. Alper, J. Am. Chem. Soc., 118, 4264 (1996); K. Okuro, H. Kai, and H. Alper, Tetrahedron: Asymmetry, 8, 2307 (1997).
7. B. G. Van den Hoven and H. Alper, J. Am. Chem. Soc., 123, 10214 (2001).
8. Examples for γ-lactams: M. Pinza, C. Farina, A. Cerri, U. Pfeiffer, M. T. Riccaboni, S. Banfi, R. Biagetti, O. Pozzi, M. Magnani, and L. Dorigotti, J. Med. Chem., 36, 4214 (1993); P. A. Reddy, B. C. H. Hsiang, T. N. Latifi, M. W. Hill, K. E. Woodward, S. M. Rothman, J. A. Ferrendelli, and D. F. Covey, J. Med. Chem., 39, 1898 (1996); A. Spaltenstein, M. R. Almond, W. J. Bock, D. G. Cleary, E. S. Furfine, R. J. Hazen, W. M. Kazmierski, F. G. Salituro, R. D. Tung, and Wright, Bioorg. Med. Chem. Lett., 10, 1159 (2000).
9. Examples for γ-lactams: M. Pinza, C. Farina, A. Cerri, U. Pfeiffer, M. T. Riccaboni, S. Banfi, R. Biagetti, O. Pozzi, M. Magnani, and L. Dorigotti, J. Med. Chem., 36, 4214 (1993); P. A. Reddy, B. C. H. Hsiang, T. N. Latifi, M. W. Hill, K. E. Woodward, S. M. Rothman, J. A. Ferrendelli, and D. F. Covey, J. Med. Chem., 39, 1898 (1996); A. Spaltenstein, M. R. Almond, W. J. Bock, D. G. Cleary, E. S. Furfine, R. J. Hazen, W. M. Kazmierski, F. G. Salituro, R. D. Tung, and Wright, Bioorg. Med. Chem. Lett., 10, 1159 (2000).
10. Examples for γ-lactams: M. Pinza, C. Farina, A. Cerri, U. Pfeiffer, M. T. Riccaboni, S. Banfi, R. Biagetti, O. Pozzi, M. Magnani, and L. Dorigotti, J. Med. Chem., 36, 4214 (1993); P. A. Reddy, B. C. H. Hsiang, T. N. Latifi, M. W. Hill, K. E. Woodward, S. M. Rothman, J. A. Ferrendelli, and D. F. Covey, J. Med. Chem., 39, 1898 (1996); A. Spaltenstein, M. R. Almond, W. J. Bock, D. G. Cleary, E. S. Furfine, R. J. Hazen, W. M. Kazmierski, F. G. Salituro, R. D. Tung, and Wright, Bioorg. Med. Chem. Lett., 10, 1159 (2000).
11. Examples for transformation of γ-lactams to γ-amino acid derivatives: P. Jouin, B. Castro, and D. Nisato, J. Chem. Soc., Perkin Trans. 1, 1987, 1177; to proline derivatives: D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, and D. J. Kempf, J. Org. Chem., 67, 5445 (2002); S. Hanessian, M. Bayrakdarian, and X. Luo, J. Am. Chem. Soc., 124, 4716 (2002); to Sceletium alkaloid: H. Ishibashi, T. S. So, K. Okochi, T. Sato, N. Nakamura, H. Nakatani, and M. Ikeda, J. Org. Chem., 56, 95 (1991).
12. Examples for transformation of γ-lactams to γ-amino acid derivatives: P. Jouin, B. Castro, and D. Nisato, J. Chem. Soc., Perkin Trans. 1, 1987, 1177; to proline derivatives: D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, and D. J. Kempf, J. Org. Chem., 67, 5445 (2002); S. Hanessian, M. Bayrakdarian, and X. Luo, J. Am. Chem. Soc., 124, 4716 (2002); to Sceletium alkaloid: H. Ishibashi, T. S. So, K. Okochi, T. Sato, N. Nakamura, H. Nakatani, and M. Ikeda, J. Org. Chem., 56, 95 (1991).
13. Examples for transformation of γ-lactams to γ-amino acid derivatives: P. Jouin, B. Castro, and D. Nisato, J. Chem. Soc., Perkin Trans. 1, 1987, 1177; to proline derivatives: D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, and D. J. Kempf, J. Org. Chem., 67, 5445 (2002); S. Hanessian, M. Bayrakdarian, and X. Luo, J. Am. Chem. Soc., 124, 4716 (2002); to Sceletium alkaloid: H. Ishibashi, T. S. So, K. Okochi, T. Sato, N. Nakamura, H. Nakatani, and M. Ikeda, J. Org. Chem., 56, 95 (1991).
14. Examples for transformation of γ-lactams to γ-amino acid derivatives: P. Jouin, B. Castro, and D. Nisato, J. Chem. Soc., Perkin Trans. 1, 1987, 1177; to proline derivatives: D. A. DeGoey, H.-J. Chen, W. J. Flosi, D. J. Grampovnik, C. M. Yeung, L. L. Klein, and D. J. Kempf, J. Org. Chem., 67, 5445 (2002); S. Hanessian, M. Bayrakdarian, and X. Luo, J. Am. Chem. Soc., 124, 4716 (2002); to Sceletium alkaloid: H. Ishibashi, T. S. So, K. Okochi, T. Sato, N. Nakamura, H. Nakatani, and M. Ikeda, J. Org. Chem., 56, 95 (1991).
15. a) K. Inomata, S. Toda, and H. Kinoshita, Chem. Lett., 1990, 1567.
16. b) S. Toda, M. Miyamoto, H. Kinoshita, and K. Inomata, Bull. Chem. Soc. Jpn., 64, 3600 (1991).
17. c) Y. Ukaji, M. Miyamoto, M. Mikuni, S. Takeuchi, and K. Inomata, Bull. Chem. Soc. Jpn., 69, 735 (1996).
18. d) S. Takeuchi, Y. Ukaji, and K. Inomata, Bull. Chem. Soc. Jpn., 74, 955 (2001).
19. Recent examples of related alkoxycarbonylation using palladium salts: Y. Tamaru, M. Hojo, and Z. Yoshida, J. Org. Chem., 56, 1099 (1991); O. Hamed, A. El-Qisairi, and P. M. Henry, J. Org. Chem., 66, 180 (2001); T. Yokota, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 67, 5005 (2002).
20. Recent examples of related alkoxycarbonylation using palladium salts: Y. Tamaru, M. Hojo, and Z. Yoshida, J. Org. Chem., 56, 1099 (1991); O. Hamed, A. El-Qisairi, and P. M. Henry, J. Org. Chem., 66, 180 (2001); T. Yokota, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 67, 5005 (2002).
21. Recent examples of related alkoxycarbonylation using palladium salts: Y. Tamaru, M. Hojo, and Z. Yoshida, J. Org. Chem., 56, 1099 (1991); O. Hamed, A. El-Qisairi, and P. M. Henry, J. Org. Chem., 66, 180 (2001); T. Yokota, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 67, 5005 (2002).
22. M. I. Bruce, J. Organomet. Chem., 44, 209 (1972).
23. Although the role of copper salt to regenerate Pd(II) species is not clear in our system, cooperative action of copper salt could be considered as described for the Wacker process: T. Hosokawa and S.-I. Murahashi, Acc. Chem. Res., 23, 49 (1990); T. Hosokawa, M. Takano, S.-I. Murahashi, H. Ozaki, Y. Kitagawa, K.-I. Sakaguchi, and Y. Katsube, J. Chem. Soc., Chem. Commun., 1994, 1433; T. Hosokawa, M. Takano, and S.-I. Murahashi, J. Am. Chem. Soc., 118, 3990 (1996).
24. Although the role of copper salt to regenerate Pd(II) species is not clear in our system, cooperative action of copper salt could be considered as described for the Wacker process: T. Hosokawa and S.-I. Murahashi, Acc. Chem. Res., 23, 49 (1990); T. Hosokawa, M. Takano, S.-I. Murahashi, H. Ozaki, Y. Kitagawa, K.-I. Sakaguchi, and Y. Katsube, J. Chem. Soc., Chem. Commun., 1994, 1433; T. Hosokawa, M. Takano, and S.-I. Murahashi, J. Am. Chem. Soc., 118, 3990 (1996).
25. Although the role of copper salt to regenerate Pd(II) species is not clear in our system, cooperative action of copper salt could be considered as described for the Wacker process: T. Hosokawa and S.-I. Murahashi, Acc. Chem. Res., 23, 49 (1990); T. Hosokawa, M. Takano, S.-I. Murahashi, H. Ozaki, Y. Kitagawa, K.-I. Sakaguchi, and Y. Katsube, J. Chem. Soc., Chem. Commun., 1994, 1433; T. Hosokawa, M. Takano, and S.-I. Murahashi, J. Am. Chem. Soc., 118, 3990 (1996).
26. At present, the reaction pathways through amine-directed hydropalladation/intramolecular carbonylation in the present monocarbonylation and amine-directed (carbomethoxy)palladation/intramolecular carbonylation in the dicarbonylation cannot be ruled out, respectively.
27. C. W. Lee and H. Alper, J. Org. Chem. 60, 250 (1995); M. E. Krafft, X. Y. Yu, and L. J. Wilson, Organometallics, 17, 2076 (1998).
28. C. W. Lee and H. Alper, J. Org. Chem. 60, 250 (1995); M. E. Krafft, X. Y. Yu, and L. J. Wilson, Organometallics, 17, 2076 (1998).
29. D. E. James and J. K. Stille, J. Am. Chem. Soc., 98, 1810 (1976).
30. R. C. Larock, H. Yang, S. M. Weinreb, and R. J. Herr, J. Org. Chem., 59, 4172 (1994).
31. Z. K. M. Abd El Samii, M. I. Al Ashmawy, and J. M. Mellor, J. Chem. Soc., Perkin Trans. 1, 1988, 2517.
32. S. Jiang, G. E. Agoston, T. Chen, M.-P. Cabal, and E. Turos, Organometallics, 14, 4697 (1995).
33. R. D. Miller and P. Goelitz, J. Org. Chem., 46, 1616 (1981).
34. C. Kaiser and J. Weinstock, Org. Synth., Coll. Vol. VI, 910 (1988).