Modification and limitations of the Livinghouse catalytic Pauson-Khand reaction

Tetrahedron Letters

Volumn 40, Issue 52, 1999, Pages 9171-9175

  Krafft, M E ^a   Bonaga, L V R ^a   Hirosawa, C ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Catalytic; Cycloaddition; Enyne; Pauson Khand reaction

Indexed keywords

ALKYNE DERIVATIVE; CARBON MONOXIDE; COBALT DERIVATIVE; CYCLOHEXYLAMINE;

ARTICLE; CATALYSIS; CATALYST; CYCLIZATION;

EID: 0033601453     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01960-7     Document Type: Article

References (28)

1. For reviews, see: (a) Pauson, P. L. Tetrahedron 1985, 41, 5855.
2. (b) Pauson, P. L. In Organometallics in Organic Synthesis. Aspects of a Modern Interdisciplinary Field; de Meijere, A.; tom Dieck, H., Eds.; Springer: Berlin, 1988; p. 233.
3. (c) Schore, N. E. Org. React. 1991, 40, 1.
4. (d) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 5, p. 1037.
5. (e) Schore, N. E. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: Oxford, 1995; Vol. 12, p. 703.
6. (f) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
7. Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
8. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
9. For the first examples of catalytic intermolecular Pauson-Khand reactions, see: Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1 1973, 977.
10. For examples of catalytic Pauson-Khand reactions using cobalt complexes, see: (a) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384.
11. (b) Rautenstrauch, V.; Megard, P.; Conesa, J.; Kuster, W. Angew. Chem., Int. Ed. Engl. 1990, 29, 1413.
12. (c) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1999, 40, 817.
13. (d) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
14. (e) Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782.
15. (f) Kim, J. W.; Chung, Y. K. Synthesis 1998, 142.
16. (g) Lee, B. Y.; Chung, Y. K.; Jeong, N.; Lee, Y.; Hwang, S. H. J. Am. Chem. Soc. 1994, 116, 8793.
17. (h) Lee, N. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145.
18. (i) Jeong, N.; Hwang, S. H.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
19. Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801.
20. Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7637.
21. Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641.
22. Entries 1, 3-7: Ref. 6. Entry 2: Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. Entries 13 and 14: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. Entry 15: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Entry 16: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. Entry 18: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
23. Entries 1, 3-7: Ref. 6. Entry 2: Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. Entries 13 and 14: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. Entry 15: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Entry 16: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. Entry 18: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
24. Entries 1, 3-7: Ref. 6. Entry 2: Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. Entries 13 and 14: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. Entry 15: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Entry 16: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. Entry 18: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
25. Entries 1, 3-7: Ref. 6. Entry 2: Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. Entries 13 and 14: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. Entry 15: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Entry 16: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. Entry 18: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
26. Entries 1, 3-7: Ref. 6. Entry 2: Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. Entries 13 and 14: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. Entry 15: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Entry 16: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. Entry 18: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
27. Entries 1, 3-7: Ref. 6. Entry 2: Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. Entries 13 and 14: Magnus, P.; Principe, L. M. Tetrahedron Lett. 1985, 26, 4851. Entry 15: Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. Entry 16: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. Entry 18: Schore, N. E.; Croudace, M. C. J. Org. Chem. 1981, 46, 5436.
28. For an alternative experimental protocol, see the accompanying communication. Krafft, M. E.; Hirosawa, C.; Bonaga, L. V. R. Tetrahedron Lett. 1999, 40, 9177.