Bicyclic carbopalladation reaction with two gem-reaction centers. Efficient construction of fused bicyclic skeletons

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9156-9157

  Ma, Shengming ^a   Xu, Bin ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; HYPOTHESIS; PHOTON; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 0032509410     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981709f     Document Type: Article

References (42)

1. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Pavoac, F.; White, C. T. In The Total Synthesis of Natural Products; Apsimon, J.; Ed.; John Wiley & Sons: New York, 1983; Vol. 5. Rigby, J. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Amsterdam, 1988; Vol. 12. Chang, C. W. J.; Scheuer, P. J. Top. Curr. Chem. 1993, 167, 33. Fraga, B. M. Nat. Prod. Rep. 1998, 15, 73. Fraga, B. M. Nat. Prod. Rep. 1995, 12, 303.
2. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Pavoac, F.; White, C. T. In The Total Synthesis of Natural Products; Apsimon, J.; Ed.; John Wiley & Sons: New York, 1983; Vol. 5. Rigby, J. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Amsterdam, 1988; Vol. 12. Chang, C. W. J.; Scheuer, P. J. Top. Curr. Chem. 1993, 167, 33. Fraga, B. M. Nat. Prod. Rep. 1998, 15, 73. Fraga, B. M. Nat. Prod. Rep. 1995, 12, 303.
3. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Pavoac, F.; White, C. T. In The Total Synthesis of Natural Products; Apsimon, J.; Ed.; John Wiley & Sons: New York, 1983; Vol. 5. Rigby, J. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Amsterdam, 1988; Vol. 12. Chang, C. W. J.; Scheuer, P. J. Top. Curr. Chem. 1993, 167, 33. Fraga, B. M. Nat. Prod. Rep. 1998, 15, 73. Fraga, B. M. Nat. Prod. Rep. 1995, 12, 303.
4. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Pavoac, F.; White, C. T. In The Total Synthesis of Natural Products; Apsimon, J.; Ed.; John Wiley & Sons: New York, 1983; Vol. 5. Rigby, J. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Amsterdam, 1988; Vol. 12. Chang, C. W. J.; Scheuer, P. J. Top. Curr. Chem. 1993, 167, 33. Fraga, B. M. Nat. Prod. Rep. 1998, 15, 73. Fraga, B. M. Nat. Prod. Rep. 1995, 12, 303.
5. Heathcock, C. H.; Graham, S. L.; Pirrung, M. C.; Pavoac, F.; White, C. T. In The Total Synthesis of Natural Products; Apsimon, J.; Ed.; John Wiley & Sons: New York, 1983; Vol. 5. Rigby, J. H. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier Science Publishers B. V.: Amsterdam, 1988; Vol. 12. Chang, C. W. J.; Scheuer, P. J. Top. Curr. Chem. 1993, 167, 33. Fraga, B. M. Nat. Prod. Rep. 1998, 15, 73. Fraga, B. M. Nat. Prod. Rep. 1995, 12, 303.
6. For most recent studies, see: Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2119. Shimoma, F.; Kondo, H.; Yuuya, S.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Nat. Prod. 1998, 61, 22. Bassett, S.; Ovenden, S. P. B.; Gable, R. W.; Capon, R. J. Aust. J. Chem. 1997, 50, 1137. Kawano, H.; Itoh, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1997, 38, 7769. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985. Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218.
7. For most recent studies, see: Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2119. Shimoma, F.; Kondo, H.; Yuuya, S.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Nat. Prod. 1998, 61, 22. Bassett, S.; Ovenden, S. P. B.; Gable, R. W.; Capon, R. J. Aust. J. Chem. 1997, 50, 1137. Kawano, H.; Itoh, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1997, 38, 7769. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985. Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218.
8. For most recent studies, see: Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2119. Shimoma, F.; Kondo, H.; Yuuya, S.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Nat. Prod. 1998, 61, 22. Bassett, S.; Ovenden, S. P. B.; Gable, R. W.; Capon, R. J. Aust. J. Chem. 1997, 50, 1137. Kawano, H.; Itoh, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1997, 38, 7769. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985. Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218.
9. For most recent studies, see: Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2119. Shimoma, F.; Kondo, H.; Yuuya, S.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Nat. Prod. 1998, 61, 22. Bassett, S.; Ovenden, S. P. B.; Gable, R. W.; Capon, R. J. Aust. J. Chem. 1997, 50, 1137. Kawano, H.; Itoh, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1997, 38, 7769. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985. Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218.
10. For most recent studies, see: Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2119. Shimoma, F.; Kondo, H.; Yuuya, S.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Nat. Prod. 1998, 61, 22. Bassett, S.; Ovenden, S. P. B.; Gable, R. W.; Capon, R. J. Aust. J. Chem. 1997, 50, 1137. Kawano, H.; Itoh, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1997, 38, 7769. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985. Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218.
11. For most recent studies, see: Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2119. Shimoma, F.; Kondo, H.; Yuuya, S.; Suzuki, T.; Hagiwara, H.; Ando, M. J. Nat. Prod. 1998, 61, 22. Bassett, S.; Ovenden, S. P. B.; Gable, R. W.; Capon, R. J. Aust. J. Chem. 1997, 50, 1137. Kawano, H.; Itoh, M.; Katoh, T.; Terashima, S. Tetrahedron Lett. 1997, 38, 7769. Harmata, M.; Carter, K. W. Tetrahedron Lett. 1997, 38, 7985. Marczak, S.; Michalak, K.; Urbanczyk-Lipkowska, Z.; Wicha, J. J. Org. Chem. 1998, 63, 2218.
12. For Pd-catalyzed syntheses of bicycles from monocycles, see: Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1977, 99, 3867. Lu, X.; Ma, S.; Ji, J.; Zhu, G.; Jiang, H. Pure Appl. Chem. 1994, 66, 1501. Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
13. For Pd-catalyzed syntheses of bicycles from monocycles, see: Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1977, 99, 3867. Lu, X.; Ma, S.; Ji, J.; Zhu, G.; Jiang, H. Pure Appl. Chem. 1994, 66, 1501. Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
14. For Pd-catalyzed syntheses of bicycles from monocycles, see: Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1977, 99, 3867. Lu, X.; Ma, S.; Ji, J.; Zhu, G.; Jiang, H. Pure Appl. Chem. 1994, 66, 1501. Ma, S.; Negishi, E. J. Am. Chem. Soc. 1995, 117, 6345.
15. For radical-initiated syntheses of bicycles from monocycles, see: Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Hayes, T. K.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533.
16. For radical-initiated syntheses of bicycles from monocycles, see: Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Hayes, T. K.; Villani, R.; Weinreb, S. M. J. Am. Chem. Soc. 1988, 110, 5533.
17. For some miscellaneous examples, see: Corey, E. J.; Nicolaou, K. C.; Melvin, L. S., Jr. J. Am. Chem. Soc. 1975, 97, 654. Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485. Corey, E. J.; Wess, G.; Xiang, Y. B.; Singh, A. K. J. Am. Chem. Soc. 1987, 109, 4717.
18. For some miscellaneous examples, see: Corey, E. J.; Nicolaou, K. C.; Melvin, L. S., Jr. J. Am. Chem. Soc. 1975, 97, 654. Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485. Corey, E. J.; Wess, G.; Xiang, Y. B.; Singh, A. K. J. Am. Chem. Soc. 1987, 109, 4717.
19. For some miscellaneous examples, see: Corey, E. J.; Nicolaou, K. C.; Melvin, L. S., Jr. J. Am. Chem. Soc. 1975, 97, 654. Corey, E. J.; Mitra, R. B.; Uda, H. J. Am. Chem. Soc. 1964, 86, 485. Corey, E. J.; Wess, G.; Xiang, Y. B.; Singh, A. K. J. Am. Chem. Soc. 1987, 109, 4717.
20. For Pauson-Khand-type formations of metal-containing bicyclic intermediates followed by CO insertion to afford bicyclic compounds, see: (a) Co: Reviews: Schore, N. E. Org. React. 1991, 40, 1. Shore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703. (b) Zr: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336. (c) Ti: Grossman, R. B.; Buchwald, S. L. J. Org. Chem. 1992, 57, 5803.
21. For Pauson-Khand-type formations of metal-containing bicyclic intermediates followed by CO insertion to afford bicyclic compounds, see: (a) Co: Reviews: Schore, N. E. Org. React. 1991, 40, 1. Shore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703. (b) Zr: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336. (c) Ti: Grossman, R. B.; Buchwald, S. L. J. Org. Chem. 1992, 57, 5803.
22. For Pauson-Khand-type formations of metal-containing bicyclic intermediates followed by CO insertion to afford bicyclic compounds, see: (a) Co: Reviews: Schore, N. E. Org. React. 1991, 40, 1. Shore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703. (b) Zr: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336. (c) Ti: Grossman, R. B.; Buchwald, S. L. J. Org. Chem. 1992, 57, 5803.
23. For Pauson-Khand-type formations of metal-containing bicyclic intermediates followed by CO insertion to afford bicyclic compounds, see: (a) Co: Reviews: Schore, N. E. Org. React. 1991, 40, 1. Shore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703. (b) Zr: Negishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336. (c) Ti: Grossman, R. B.; Buchwald, S. L. J. Org. Chem. 1992, 57, 5803.
24. For some most recent studies on methodologies for the synthesis of bicyclic compounds, see: (a) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335.
25. For some most recent studies on methodologies for the synthesis of bicyclic compounds, see: (a) Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940. (b) Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335.
26. Ma, S. Youji Huaxue 1991, 11, 561.
27. (b) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
28. (c) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev. 1996, 96, 365.
29. For the formation of alkylidenecarbenes from 1,1-dibromoalk-1-enes via α-dehalometalation reactions, see: (a) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (b) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (c) Harada, T.; Hara, D.; Hattori, K.; Oku, A. Tetrahedron Lett. 1988, 29, 3821.
30. For the formation of alkylidenecarbenes from 1,1-dibromoalk-1-enes via α-dehalometalation reactions, see: (a) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (b) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (c) Harada, T.; Hara, D.; Hattori, K.; Oku, A. Tetrahedron Lett. 1988, 29, 3821.
31. For the formation of alkylidenecarbenes from 1,1-dibromoalk-1-enes via α-dehalometalation reactions, see: (a) Kunishima, M.; Hioki, K.; Ohara, T.; Tani, S. J. Chem. Soc., Chem. Commun. 1992, 219. (b) Kunishima, M.; Hioki, K.; Tani, S.; Kato, A. Tetrahedron Lett. 1994, 35, 7253. (c) Harada, T.; Hara, D.; Hattori, K.; Oku, A. Tetrahedron Lett. 1988, 29, 3821.
32. For monocyclic carbopalladation of gem-dibromides, see: Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243. Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991. Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A. Tetrahedron Lett. 1993, 34, 2139.
33. For monocyclic carbopalladation of gem-dibromides, see: Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243. Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991. Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A. Tetrahedron Lett. 1993, 34, 2139.
34. For monocyclic carbopalladation of gem-dibromides, see: Nuss, J. M.; Levine, B. H.; Rennels, R. A.; Heravi, M. M. Tetrahedron Lett. 1991, 32, 5243. Nuss, J. M.; Rennels, R. A.; Levine, B. H. J. Am. Chem. Soc. 1993, 115, 6991. Torii, S.; Okumoto, H.; Tadokoro, T.; Nishimura, A.; Rashid, M. A. Tetrahedron Lett. 1993, 34, 2139.
35. All the starting compounds were synthesized by the sequential alkylation of dimethyl malonate with 1,1,3-tribromo-2-(bromomethyl)-propene and the corresponding alkenyl bromides or the reaction of allyl alcohol with 1,1,3-tribromo-2-(bromomethyl)propene in the presence of NaH in THF.
36. For phase transfer-catalyzed intermolecular Heck reactions in DMF, see: Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667. Jeffery, T. Synthesis 1987, 70.
37. For phase transfer-catalyzed intermolecular Heck reactions in DMF, see: Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667. Jeffery, T. Synthesis 1987, 70.
38. For phase transfer-catalyzed intermolecular Heck reactions in DMF, see: Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667. Jeffery, T. Synthesis 1987, 70.
39. max = 55.0°C, 1491 reflections with I > 3.00σ-(I) were used in the refinement, R = 0.056.
40. For the formation of seven-membered rings via an exo-mode cyclic carbopalladation reaction of benzylic halides, see: Wu, G.; Lamaty, F.; Negishi, E. J. Org. Chem. 1989, 54, 2507. (b) For the formation of seven-membered rings via an exo-mode cyclic carbopalladation reaction of aryl halides and an endo-mode cyclic carbopalladation of alkenyl halides, see: Negishi, E.; Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922.
41. For the formation of seven-membered rings via an exo-mode cyclic carbopalladation reaction of benzylic halides, see: Wu, G.; Lamaty, F.; Negishi, E. J. Org. Chem. 1989, 54, 2507. (b) For the formation of seven-membered rings via an exo-mode cyclic carbopalladation reaction of aryl halides and an endo-mode cyclic carbopalladation of alkenyl halides, see: Negishi, E.; Ma, S.; Sugihara, T.; Noda, Y. J. Org. Chem. 1997, 62, 1922.
42. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.