Bicyclization of enynes using the Cp2TiCl2-Mg-BTC system: A practical method to bicyclic cyclopentenones

Journal of Organic Chemistry

Volumn 63, Issue 25, 1998, Pages 9285-9291

  Zhao, Zongbao ^a   Ding, Yu ^a   Zhao, Gang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; CYCLOPENTENONE DERIVATIVE; TITANIUM DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032509383     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9810718     Document Type: Article

References (70)

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2. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elservier Press: New York, 1995; Vol. 12, p 703. For recent examples of this reaction, see: (c) Ahmar, M.; Locatelli, C.; Colombier, D.; Cazes, B. Tetrahedron Lett. 1997, 38, 5281. (d) Jordi, L.; Ricart, S.; Vinas, J. M.; Moretó, J. M. Organometallics 1997, 16, 2808.
3. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elservier Press: New York, 1995; Vol. 12, p 703. For recent examples of this reaction, see: (c) Ahmar, M.; Locatelli, C.; Colombier, D.; Cazes, B. Tetrahedron Lett. 1997, 38, 5281. (d) Jordi, L.; Ricart, S.; Vinas, J. M.; Moretó, J. M. Organometallics 1997, 16, 2808.
4. For reviews, see: (a) Schore, N. E. Org. React. 1991, 40, 1. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G., Wilkinson, G., Eds.; Elservier Press: New York, 1995; Vol. 12, p 703. For recent examples of this reaction, see: (c) Ahmar, M.; Locatelli, C.; Colombier, D.; Cazes, B. Tetrahedron Lett. 1997, 38, 5281. (d) Jordi, L.; Ricart, S.; Vinas, J. M.; Moretó, J. M. Organometallics 1997, 16, 2808.
5. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
6. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
7. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
8. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
9. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
10. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
11. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
12. For effecting this reaction using dry-state adsorption techniques, see: (a) Smit, W. A.; Kireev, S. L.; Nefedov, O. M.; Tarasov, V. A. Tetrahedron Lett. 1989, 30, 4021. (b) Smit, W. A.; Gybin, A. S.; Simonyan, S. O.; Shashkov, A. S.; Tarasov, Y. T.; Strychkov, Y. T.; Kyz'mina, L. G.; Mikaelian, G. S.; Cable, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241. For effecting this reaction using various additives, see: (c) Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289. (d) Kraft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199. (e) Billington, D. C.; Helps, I. M.; Pauson, P. L.; Thomson, W.; Willison, D. J. Organomet. Chem. 1988, 354, 233. (f) Chung, Y. K.; Lee, B. Y.; Jeong, N.; Hudecek, M.; Pauson, P. L. Organometallics 1993, 12, 220. (g) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. (h) Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
13. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
14. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
15. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
16. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
17. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
18. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
19. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
20. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
21. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
22. For Fe, see: (a) Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656. (b) Knolker, H. J.; Heber, J. Synlett 1993, 924. (c) Pearson, A. J.; Yao, X. Synlett 1997, 1281. (d) Pearson, A. J.; Dubbert, R. A. J. Chem. Soc., Chem. Commun. 1991, 202. For W, see: (e) Hoye, T. R.; Suriano, J. A. J. Am. Chem. Soc. 1993, 115, 1154. For Cr, see: (f) Jordi, L.; Segundo, A.; Camps, F.; Ricart, S.; Moreto, J. M. Organometallics 1993, 12, 3795. For Mo, see: (g) Jeong, N.; Lee, S. J.; Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1993, 34, 4027. For Ni, see: (h) Tamao, K.; Kobayashi, K.; Ito, Y. J. Am. Chem. Soc. 1988, 110, 1286. (i) Tamao, K.; Kobayashi, K.; Ito, Y. Synlett 1992, 539. (j) Buchwald, S. L.; Zhang, M. J. Org. Chem. 1996, 61, 4498. For Ru, Rh, Ti, see ref 18.
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48. (a) The exact structure like 10 is unknown; however, any other alternatives should keep the retention of stereochemistry from titanacycle to final product in mind. A simliar seven-membered ring intermediate involving a titanium-oxygen bond has also been suggested by Sato. Gao, Y.; Shirai, M.; Sato, F. Tetrahedron Lett. 1997, 38, 6849.
49. (b) One alternative may be an intermediate like Y, which is what we thought in the early stage of this work. However, the stereochemistry outcome of this reaction indicates something contradictory with intermediate Y, since an open chain intermediate will most probably fail to give good stereoselectivity. (Equation Presented)
50. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
51. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
52. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
53. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
54. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
55. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
56. A catalytic Pauson-Khand reaction is currently available with different metal complexes. For Co, see: (a) Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159. (b) Pagenkopf, B.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285. For Ru, see: (c) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762. (d) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187. For Rh, see: (e) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249. For Ti, see ref 6c. An enantioselective catalytic Pauson-Khand- type reaction using titanocene dicarbonyl complex is also known. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688. A catalytic Pauson-Khand reaction in super critical carbon dioxide has been developed. Jeong, N.; Hwang, S. E.; Lee, Y. W.; Lim, J. S. J. Am. Chem. Soc. 1997, 119, 10549.
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