Studies on [PdH]- and [PdCl]-catalyzed intramolecular cyclization: The search for a better solution to selective enyne coupling

Organometallics

Volumn 15, Issue 12, 1996, Pages 2821-2828

  Ji, Jianguo ^a   Wang, Zhong ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000539687     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om960022n     Document Type: Article

References (65)

1. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Boyd, G. V. In The Ene Reaction in Chemistry of Double-Bonded Functional Groups; Patai, S. Ed.; Wiley: Chichester, U.K., 1989; part 2, p 477.
2. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Boyd, G. V. In The Ene Reaction in Chemistry of Double-Bonded Functional Groups; Patai, S. Ed.; Wiley: Chichester, U.K., 1989; part 2, p 477.
3. Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem. 1989, 101, 1559. Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390. Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
4. Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem. 1989, 101, 1559. Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390. Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
5. Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem. 1989, 101, 1559. Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390. Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
6. Trost, B. M.; Hipskind, P. A.; Chung, J. Y. L.; Chan, C. Angew. Chem. 1989, 101, 1559. Wender, P. A.; Keenan, R. M.; Lee, H. Y. J. Am. Chem. Soc. 1987, 109, 4390. Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087. Ji, J.; Zhang, C.; Lu, X. J. Org. Chem. 1995, 60, 1160.
7. (a) Trost, B. M.; Lautens, M. J. Am. Chem. Soc. 1985, 107, 1781.
8. (b) Trost, B. M.; Macpherson, D. T. J. Am. Chem. Soc. 1987, 109, 3483.
9. (c) Trost, B. M.; Phan, L. T. Tetrahedron Lett. 1993, 34, 4735. For a review see: Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
10. (c) Trost, B. M.; Phan, L. T. Tetrahedron Lett. 1993, 34, 4735. For a review see: Trost, B. M. Acc. Chem. Res. 1990, 23, 34.
11. (a) Ma, S. Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733.
12. (b) Ma, S.; Lu, X. J. Org. Chem. 1991, 56, 5120.
13. (c) Ma, S.; Lu, X. J. Org. Chem. 1993, 58, 1245.
14. (d) Ji, J.; Lu, X. Synlett 1993, 745.
15. (a) Lu, X.; Zhu, G. Synlett 1993, 68.
16. (b) Bäckvall, J.-E.; Nilsson, Y. I. M.; Andersson, P. G.; Gatti, R. G. P.; Wu, J. Tetrahedron Lett. 1994, 35, 5713.
17. (a) Tsubuki, M.; Kanai, K.; Keino, K.; Kakinuma, N.; Honda, T. J. Org. Chem. 1992, 57, 2930.
18. (b) Glotter, E, Nat. Prod. Rep. 1991, 8, 415.
19. Romeyke, Y.; Keller, M.; Kluge, H.; Grabley, S.; Hammann, P. Tetrahedron 1991, 47, 3335. Bomoni, C.; Pucci, P.; Racioppi, R.; Viggiani, L. Tetrahedron: Asymmetry 1992, 3, 29. Cavill, G. W. K.; Clark, D. V.; Whitefield, F. B. Aust. J. Chem. 1968, 21, 2819.
20. Romeyke, Y.; Keller, M.; Kluge, H.; Grabley, S.; Hammann, P. Tetrahedron 1991, 47, 3335. Bomoni, C.; Pucci, P.; Racioppi, R.; Viggiani, L. Tetrahedron: Asymmetry 1992, 3, 29. Cavill, G. W. K.; Clark, D. V.; Whitefield, F. B. Aust. J. Chem. 1968, 21, 2819.
21. Romeyke, Y.; Keller, M.; Kluge, H.; Grabley, S.; Hammann, P. Tetrahedron 1991, 47, 3335. Bomoni, C.; Pucci, P.; Racioppi, R.; Viggiani, L. Tetrahedron: Asymmetry 1992, 3, 29. Cavill, G. W. K.; Clark, D. V.; Whitefield, F. B. Aust. J. Chem. 1968, 21, 2819.
22. Mazur, P.; Nakanishi, K. J. Org. Chem. 1992, 57, 1047.
23. Ohloff, G. Prog. Chem. Org. Nat. Prod. 1978, 35, 431. Brand, J. M.; Yuong, J.; Silverstein, R. M. Prog. Chem. Org. Nat. Prod. 1979, 37, 1. Dickinson, J. M. Nat. Prod. Rep. 1993, 10, 71.
24. Ohloff, G. Prog. Chem. Org. Nat. Prod. 1978, 35, 431. Brand, J. M.; Yuong, J.; Silverstein, R. M. Prog. Chem. Org. Nat. Prod. 1979, 37, 1. Dickinson, J. M. Nat. Prod. Rep. 1993, 10, 71.
25. Ohloff, G. Prog. Chem. Org. Nat. Prod. 1978, 35, 431. Brand, J. M.; Yuong, J.; Silverstein, R. M. Prog. Chem. Org. Nat. Prod. 1979, 37, 1. Dickinson, J. M. Nat. Prod. Rep. 1993, 10, 71.
26. Mulzer, J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, U. K., 1991; Vol. 6, p 324. Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
27. Mulzer, J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, U. K., 1991; Vol. 6, p 324. Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
28. Mulzer, J. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I. Eds.; Pergamon Press: Oxford, U. K., 1991; Vol. 6, p 324. Hoffman, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94. Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157.
29. For recent progress see: Tsubiki, M.; Kanai, K.; Honda, T. Heterocycles 1993, 35, 281. Schink, H. E.; Bäckvall, J.-E. J. Org. Chem. 1992, 57, 1588. Pilli, R. A.; Murta, M. M. J. Org. Chem. 1993, 58, 338. Carcamo, C. Fajardo, V.; Tojo, E. Heterocycles 1993, 36, 1771.
30. For recent progress see: Tsubiki, M.; Kanai, K.; Honda, T. Heterocycles 1993, 35, 281. Schink, H. E.; Bäckvall, J.-E. J. Org. Chem. 1992, 57, 1588. Pilli, R. A.; Murta, M. M. J. Org. Chem. 1993, 58, 338. Carcamo, C. Fajardo, V.; Tojo, E. Heterocycles 1993, 36, 1771.
31. For recent progress see: Tsubiki, M.; Kanai, K.; Honda, T. Heterocycles 1993, 35, 281. Schink, H. E.; Bäckvall, J.-E. J. Org. Chem. 1992, 57, 1588. Pilli, R. A.; Murta, M. M. J. Org. Chem. 1993, 58, 338. Carcamo, C. Fajardo, V.; Tojo, E. Heterocycles 1993, 36, 1771.
32. For recent progress see: Tsubiki, M.; Kanai, K.; Honda, T. Heterocycles 1993, 35, 281. Schink, H. E.; Bäckvall, J.-E. J. Org. Chem. 1992, 57, 1588. Pilli, R. A.; Murta, M. M. J. Org. Chem. 1993, 58, 338. Carcamo, C. Fajardo, V.; Tojo, E. Heterocycles 1993, 36, 1771.
33. Yamamoto, A. Organotransition Metal Chemistry; Wiley: New York, 1986; p 233. Hayashi, Y.; Yamamoto, T.; Yamamoto, A.; Komiya, S.; Kushi, Y. J. Am. Chem. Soc. 1986, 108, 385.
34. Yamamoto, A. Organotransition Metal Chemistry; Wiley: New York, 1986; p 233. Hayashi, Y.; Yamamoto, T.; Yamamoto, A.; Komiya, S.; Kushi, Y. J. Am. Chem. Soc. 1986, 108, 385.
35. Long chain alkynoates such as Ie may isomerize to dienes in the presence of [PdH] species, which might further induce side reactions leading to a complex mixture of products. See: (a) Ma, D.; Yu; Y.; Lu, X. J. Org. Chem. 1989, 54, 1105. (b) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2303. (c) Guo. C.; Lu, X. J. Chem. Soc., Perkin Trans, 1 1993, 1921.
36. Long chain alkynoates such as Ie may isomerize to dienes in the presence of [PdH] species, which might further induce side reactions leading to a complex mixture of products. See: (a) Ma, D.; Yu; Y.; Lu, X. J. Org. Chem. 1989, 54, 1105. (b) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2303. (c) Guo. C.; Lu, X. J. Chem. Soc., Perkin Trans, 1 1993, 1921.
37. Long chain alkynoates such as Ie may isomerize to dienes in the presence of [PdH] species, which might further induce side reactions leading to a complex mixture of products. See: (a) Ma, D.; Yu; Y.; Lu, X. J. Org. Chem. 1989, 54, 1105. (b) Trost, B. M.; Schmidt, T. J. Am. Chem. Soc. 1988, 110, 2303. (c) Guo. C.; Lu, X. J. Chem. Soc., Perkin Trans, 1 1993, 1921.
38. Bachi, M. D.; Bosch, E. J. Org. Chem. 1992, 57, 4696 and references cited therein.
39. James, B. P. In Comprehensive Organometallic Chemistry, Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 8, p 285. Siegel, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, p 417.
40. James, B. P. In Comprehensive Organometallic Chemistry, Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Vol. 8, p 285. Siegel, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 8, p 417.
41. Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914. Huggin, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002. Rice, N. C.; Oliver, J. D. J. Organomet. Chem. 1978, 145, 121. Hine, K. E.; Clark, H. C. J. Organomet. Chem. 1976, 105, C32.
42. Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914. Huggin, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002. Rice, N. C.; Oliver, J. D. J. Organomet. Chem. 1978, 145, 121. Hine, K. E.; Clark, H. C. J. Organomet. Chem. 1976, 105, C32.
43. Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914. Huggin, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002. Rice, N. C.; Oliver, J. D. J. Organomet. Chem. 1978, 145, 121. Hine, K. E.; Clark, H. C. J. Organomet. Chem. 1976, 105, C32.
44. Zargarian, D.; Alper, H. Organometallics 1991, 10, 2914. Huggin, J. M.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 3002. Rice, N. C.; Oliver, J. D. J. Organomet. Chem. 1978, 145, 121. Hine, K. E.; Clark, H. C. J. Organomet. Chem. 1976, 105, C32.
45. Blackmore, T.; Bruce, M. I.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1974, 106.
46. Hart, D. W.; Schwartz, J. J. Organomet. Chem. 1975, 85, C11.
47. (a) Dietl, H.; Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 2, p 47.
48. (a) Dietl, H.; Reinheimer, H.; Moffat, J.; Maitlis, P. M. J. Am. Chem. Soc. 1970, 92, 2276. Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 2, p 47.
49. (b) Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
50. (c) Bäckvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
51. Marshall, P. R. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. l, p 170. Green, R. H.; Lambert, P. F.; Newton, R. F.; Roberts, S. M. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. 3, p 107. Trost, B. M. Chem. Soc. Rev. 1981, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
52. Marshall, P. R. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. l, p 170. Green, R. H.; Lambert, P. F.; Newton, R. F.; Roberts, S. M. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. 3, p 107. Trost, B. M. Chem. Soc. Rev. 1981, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
53. Marshall, P. R. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. l, p 170. Green, R. H.; Lambert, P. F.; Newton, R. F.; Roberts, S. M. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. 3, p 107. Trost, B. M. Chem. Soc. Rev. 1981, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
54. Marshall, P. R. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. l, p 170. Green, R. H.; Lambert, P. F.; Newton, R. F.; Roberts, S. M. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. 3, p 107. Trost, B. M. Chem. Soc. Rev. 1981, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
55. Marshall, P. R. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. l, p 170. Green, R. H.; Lambert, P. F.; Newton, R. F.; Roberts, S. M. In Aliphatic and Related Natural Product Chemistry; Burlinton: London, 1979; Vol. 3, p 107. Trost, B. M. Chem. Soc. Rev. 1981, 11, 141. Ramaiah, M. Synthesis 1984, 529. Paquette, L. A. Top. Curr. Chem. 1984, 119, 1.
56. Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969. Davies, H. M. L.; Clark, T. J.; Church, L. A. Tetrahedron Lett. 1989, 30, 5057.
57. Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969. Davies, H. M. L.; Clark, T. J.; Church, L. A. Tetrahedron Lett. 1989, 30, 5057.
58. Elimination and inverse readdition of metal hydride species to carbon-carbon multiple bonds were substantially documented: Wilkinson, G.; Stone, F. G. A.; Abel, W. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982. Trost, B. M.; Schmidt, T. J Am. Chem. Soc. 1988, 110, 2301. Ma, D.; Yu, Y.; Lu, X. J. Org. Chem. 1989, 54, 1105.
59. Elimination and inverse readdition of metal hydride species to carbon-carbon multiple bonds were substantially documented: Wilkinson, G.; Stone, F. G. A.; Abel, W. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982. Trost, B. M.; Schmidt, T. J Am. Chem. Soc. 1988, 110, 2301. Ma, D.; Yu, Y.; Lu, X. J. Org. Chem. 1989, 54, 1105.
60. Elimination and inverse readdition of metal hydride species to carbon-carbon multiple bonds were substantially documented: Wilkinson, G.; Stone, F. G. A.; Abel, W. Comprehensive Organometallic Chemistry; Pergamon: Oxford, U.K., 1982. Trost, B. M.; Schmidt, T. J Am. Chem. Soc. 1988, 110, 2301. Ma, D.; Yu, Y.; Lu, X. J. Org. Chem. 1989, 54, 1105.
61. Ma, S.; Lu, X. Unpublished results.
62. Maitlis, P. M. The Organic Chemistry of Palladium; Academic Press: New York, 1971; Vol. 2, p 137.
63. Stephenson, T. A.; Morehouse, S. M.; Powell, A. R.; Heffer, J. P.; Wilkinson, G. J. Chem. Soc. 1965, 3632.
64. 2 (Brandsma, L. Preparative Acetylenic Chemistry, 2nd ed.; Elsevier: Amsterdam, 1988; p 100).
65. Kanai, K, Sakamoto, I.; Ogawa, S.; Suami, T. Bull. Chem. Soc. Jpn. 1987, 60, 1529.