Titanium(IV) aryloxide catalyzed cyclization reactions of 1,6- and 1,7- dienes [5]

Journal of the American Chemical Society

Volumn 122, Issue 6, 2000, Pages 1223-1224

  Okamoto, Sentaro ^a   Livinghouse, Tom ^a  

^a MONTANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; TITANIUM DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; ISOMERISM; LETTER; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0034673335     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9922680     Document Type: Letter

References (48)

1. (a) Yasuda, H.; Nakamura, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 723. Buchwald, S. L.; Neilsen, R. B. Chem. Rev. 1988, 88, 1047.
2. (a) Yasuda, H.; Nakamura, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 723. Buchwald, S. L.; Neilsen, R. B. Chem. Rev. 1988, 88, 1047.
3. (b) Negishi, E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 1163.
4. (c) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111. See also ref 3q.
5. (c) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111. See also ref 3q.
6. (c) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111. See also ref 3q.
7. (c) Broene, R. D.; Buchwald, S. L. Science 1993, 261, 1696. Negishi, E.; Takahashi, T. Acc. Chem. Res. 1994, 27, 124. Hanzawa, Y.; Ito, H.; Taguchi, T. Synlett 1995, 299. Ohff, A.; Pulst, S.; Lefeber, C.; Peulecke, N.; Arndt, P.; Burkalov, V. V.; Rosenthal, U. Synlett 1996, 111. See also ref 3q.
8. 2Cl in synthesis, see: Fairfax, D.; Stein, M.; Livinghouse, T. Organometallics, 1997, 16, 1523. McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485 and references therein.
9. 2Cl in synthesis, see: Fairfax, D.; Stein, M.; Livinghouse, T. Organometallics, 1997, 16, 1523. McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485 and references therein.
10. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
11. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
12. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
13. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
14. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
15. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
16. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
17. 2: (g) Johnson, E. S.; Balaich, G. J.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 7685. (h) Johnson, E. S.; Balich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086 and see also ref 7.
18. 3 Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Prityrskaya, T. S. Zh. Org. Khim. 1991, 27, 294. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. See also: Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413 and refs 5a,b,e.
19. 3 Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Prityrskaya, T. S. Zh. Org. Khim. 1991, 27, 294. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. See also: Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413 and refs 5a,b,e.
20. 3 Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Prityrskaya, T. S. Zh. Org. Khim. 1991, 27, 294. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. See also: Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413 and refs 5a,b,e.
21. 3 Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Pritytskaya, T. S. Zh. Org. Khim. 1989, 25, 2244. Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A.; Savchenko, A. I.; Prityrskaya, T. S. Zh. Org. Khim. 1991, 27, 294. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1995, 117, 9919. See also: Chaplinski, V.; de Meijere, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 413 and refs 5a,b,e.
22. n equivalent in the synthesis of cyclopropanols, see: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234. (b) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428. For catalytic cyclo-bis-zincation of enynes, see: (c) Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. For catalytic carbometalation of dienes, see: (d) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. For ligand modification leading to optically enriched cyclopropanols, see: (e) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
23. n equivalent in the synthesis of cyclopropanols, see: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234. (b) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428. For catalytic cyclo-bis-zincation of enynes, see: (c) Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. For catalytic carbometalation of dienes, see: (d) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. For ligand modification leading to optically enriched cyclopropanols, see: (e) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
24. n equivalent in the synthesis of cyclopropanols, see: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234. (b) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428. For catalytic cyclo-bis-zincation of enynes, see: (c) Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. For catalytic carbometalation of dienes, see: (d) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. For ligand modification leading to optically enriched cyclopropanols, see: (e) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
25. n equivalent in the synthesis of cyclopropanols, see: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234. (b) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428. For catalytic cyclo-bis-zincation of enynes, see: (c) Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. For catalytic carbometalation of dienes, see: (d) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. For ligand modification leading to optically enriched cyclopropanols, see: (e) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
26. n equivalent in the synthesis of cyclopropanols, see: (a) Kulinkovich, O. G.; Sviridov, S. V.; Vasilevskii, D. A. Synthesis 1991, 234. (b) Kulinkovich, O. G.; Vasilevskii, D. A.; Savchenko, A. I.; Sviridov, S. V. Zh. Org. Khim. 1991, 27, 1428. For catalytic cyclo-bis-zincation of enynes, see: (c) Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. For catalytic carbometalation of dienes, see: (d) Negishi, E.; Jensen, M. D.; Kondakov, D. Y.; Wang, S. J. Am. Chem. Soc. 1994, 116, 8404. For ligand modification leading to optically enriched cyclopropanols, see: (e) Corey, E. J.; Rao, S. A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 9345.
27. 3 and 5 equiv of Grignard reagents: Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
28. 3 and 5 equiv of Grignard reagents: Lee, J.; Kang, C. H.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 291. Lee, J.; Kim, H.; Cha, J. K. J. Am. Chem. Soc. 1996, 118, 4198.
29. 4Ti was prepared by a modification of the literature procedure: Durfee, L. D.; Latesky, S. L.; Rothwell, I. P.; Huffman, J. C.; Folting, K. Inorg. Chem. 1985, 24, 4569.
30. 2, 2BuLi, and 1,7-octadiene, but this titanacycle could not catalyze the cyclization of 1,6-heptadiene: Waratuke, S. A.; Thorn, M. G.; Hill, J. E.; Waratuke, A. S.; Johnson, E. S.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630 and references therein.
31. Titanocene derivative-catalyzed cyclization of enynes and alkenones has been reported: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424. Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
32. Titanocene derivative-catalyzed cyclization of enynes and alkenones has been reported: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424. Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
33. Titanocene derivative-catalyzed cyclization of enynes and alkenones has been reported: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424. Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
34. Titanocene derivative-catalyzed cyclization of enynes and alkenones has been reported: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424. Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
35. Titanocene derivative-catalyzed cyclization of enynes and alkenones has been reported: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424. Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
36. Titanocene derivative-catalyzed cyclization of enynes and alkenones has been reported: Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 5818; Kablaoui, N. M.; Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 4424. Montchamp, J.-L.; Negishi, E. J. Am. Chem. Soc. 1998, 120, 5345. Sturla, S. J.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 1976.
37. 4Ti and 50 mol % of cyc-HexMgCl did not give cyclized product. In initial investigations, we found that the reaction could be carried out by using i-PrMgCl, i-BuMgCl, n-BuMgBr, or cyc-HexMgCl. Among these activators, cyc-HexMgCl gave slightly better yields. The use of EtMgBr did not provide cyclized product.
38. 2, see refs 3-7.
39. (a) Akita, M.; Yasuda, H.; Nagasuna, K.; Nakamura, A. Bull. Chem. Soc. Jpn. 1983, 56, 554 and references therein.
40. 4Ti/ RMgCl-catalyzed diene cyclizations is therefore inconsistent with the participation of a Ti(III) intermediate in the catalyic cycle. (Equation presented)
41. A similar mechanism to explain the formation of 2-methyl-1-methylenecycloalkanes from bicyclometallacyclopentenes has been discussed: (a) Smith, G.; McLain, S. J.; Schrock, R. R. J. Organomet. Chem. 1980, 202, 269. (b) Yamamoto, Y.; Ohkoshi, N.; Kameda, M.; Itoh, K. J. Org. Chem. 1999, 64, 2178, and refs 7 and 13.
42. A similar mechanism to explain the formation of 2-methyl-1- methylenecycloalkanes from bicyclometallacyclopentenes has been discussed: (a) Smith, G.; McLain, S. J.; Schrock, R. R. J. Organomet. Chem. 1980, 202, 269. (b) Yamamoto, Y.; Ohkoshi, N.; Kameda, M.; Itoh, K. J. Org. Chem. 1999, 64, 2178, and refs 7 and 13.
43. Thermal decomposition of bicyclic titana- and zirconacyclopentanes to provide 2-methyl-1-methylenecycloalkanes has been reported: McDermott, J. X.; Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6529. Takahashi, T.; Kotora, M.; Kasai, K. J. Chem. Soc., Chem. Commun. 1994, 2693.
44. Thermal decomposition of bicyclic titana- and zirconacyclopentanes to provide 2-methyl-1-methylenecycloalkanes has been reported: McDermott, J. X.; Wilson, M. E.; Whitesides, G. M. J. Am. Chem. Soc. 1976, 98, 6529. Takahashi, T.; Kotora, M.; Kasai, K. J. Chem. Soc., Chem. Commun. 1994, 2693.
45. For additional examples of transition metal-catalyzed cycloisomerization of 1,6-dienes, see: Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007. Heumann, A.; Moukhliss, M. Synlett 1998, 1211. Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715. Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bewcaw, J. E. Synlett 1990, 74.
46. For additional examples of transition metal-catalyzed cycloisomerization of 1,6-dienes, see: Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007. Heumann, A.; Moukhliss, M. Synlett 1998, 1211. Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715. Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bewcaw, J. E. Synlett 1990, 74.
47. For additional examples of transition metal-catalyzed cycloisomerization of 1,6-dienes, see: Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007. Heumann, A.; Moukhliss, M. Synlett 1998, 1211. Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715. Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bewcaw, J. E. Synlett 1990, 74.
48. For additional examples of transition metal-catalyzed cycloisomerization of 1,6-dienes, see: Radetich, B.; RajanBabu, T. V. J. Am. Chem. Soc. 1998, 120, 8007. Heumann, A.; Moukhliss, M. Synlett 1998, 1211. Christoffers, J.; Bergman, R. G. J. Am. Chem. Soc. 1996, 118, 4715. Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bewcaw, J. E. Synlett 1990, 74.