Preparation of 1,2,3-trisubstituted cyclopentadienes and tetrahydroindene derivatives from zircoanacyclopentenes

Tetrahedron Letters

Volumn 37, Issue 42, 1996, Pages 7521-7524

  Takahashi, Tamotsu ^a   Xi, Zhenfeng ^a   Kotora, Martin ^a   Xi, Chanjuan ^a   Nakajima, Kiyohiko ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b AICHI UNIVERSITY OF EDUCATION   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTADIENE DERIVATIVE; INDENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030583499     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01689-9     Document Type: Article

References (18)

1. 1. (a) Takahashi, T.; Kageyama, M.; Denisov, V.; Hara, R.; Negishi, E. Tetrahedron Lett. 1993, 34, 687-690;
2. (b) Takahashi, T.; Xi, Z.; Rousset, C. J.; Suzuki, N. Chem. Lett. 1993, 1001-1004;
3. (c) Xi, Z.; Hara, R.; Takahashi, T. J. Org. Chem. 1995, 60, 4444-4448.
4. 2. For reviews on the synthesis and applications of cyclopentadienyl ligands, see: (a) Okuda, J. Top. Curr. Chem. 1991, 160, 97-145. (b) Halterman, R. L. Chem. Rev. 1992, 92, 965-994.
5. For reviews on the synthesis and applications of cyclopentadienyl ligands, see: (a) Okuda, J. Top. Curr. Chem. 1991, 160, 97-145. (b) Halterman, R. L. Chem. Rev. 1992, 92, 965-994.
6. 3. For reviews on metallocene-catalyzed polymerization, see: (a) Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Kaminsky, W.; Sinn, H. Eds.; Springer-Verlag: Berlin and Heiderberg, 1988; (b) Transition Metal Catalyzed Polymerizations: Ziegler-Natta and Metathesis Polymerizations; Quirk, R. P. Ed.; Cambridge University Press: Cambridge, 1988; (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325; (d) Coates, G. W.; Waymouth, R. M. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L.S. Eds.; Pergamon Press: Oxford, U. K., 1995; Vol. 12, Chapter 12, pp. 1193-1208. and references therein.
7. For reviews on metallocene-catalyzed polymerization, see: (a) Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Kaminsky, W.; Sinn, H. Eds.; Springer-Verlag: Berlin and Heiderberg, 1988; (b) Transition Metal Catalyzed Polymerizations: Ziegler-Natta and Metathesis Polymerizations; Quirk, R. P. Ed.; Cambridge University Press: Cambridge, 1988; (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325; (d) Coates, G. W.; Waymouth, R. M. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L.S. Eds.; Pergamon Press: Oxford, U. K., 1995; Vol. 12, Chapter 12, pp. 1193-1208. and references therein.
8. For reviews on metallocene-catalyzed polymerization, see: (a) Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Kaminsky, W.; Sinn, H. Eds.; Springer-Verlag: Berlin and Heiderberg, 1988; (b) Transition Metal Catalyzed Polymerizations: Ziegler-Natta and Metathesis Polymerizations; Quirk, R. P. Ed.; Cambridge University Press: Cambridge, 1988; (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325; (d) Coates, G. W.; Waymouth, R. M. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L.S. Eds.; Pergamon Press: Oxford, U. K., 1995; Vol. 12, Chapter 12, pp. 1193-1208. and references therein.
9. For reviews on metallocene-catalyzed polymerization, see: (a) Transition Metals and Organometallics as Catalysts for Olefin Polymerization, Kaminsky, W.; Sinn, H. Eds.; Springer-Verlag: Berlin and Heiderberg, 1988; (b) Transition Metal Catalyzed Polymerizations: Ziegler-Natta and Metathesis Polymerizations; Quirk, R. P. Ed.; Cambridge University Press: Cambridge, 1988; (c) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325; (d) Coates, G. W.; Waymouth, R. M. in Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G.; Hegedus, L.S. Eds.; Pergamon Press: Oxford, U. K., 1995; Vol. 12, Chapter 12, pp. 1193-1208. and references therein.
10. 4. Lee, B. Y.; Moon, H.; Chung, Y. K.; Jeong, N. J. Am. Chem. Soc. 1994, 116, 2163-2164.
11. 5. (a) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Organometallics 1994, 13, 4183-4185.
12. (b) Kasai, K.; Kotora, M.; Suzuki, N.; Takahashi, T. J. Chem. Soc., Chem. Commun., 1995, 109-110.
13. 2ZrRCl, have been reported to react with acid chloride in the presence of a catalytic amount of copper salts. see: Wipf, P.; Xu, W. Synlett. 1992, 718-721; However, in most cases, especially in the case of zirconacycles, acylation reactions do not occur without transmetallation to Cu.
14. 7. Takahashi, T.; Kotora, M.; Xi, Z. J. Chem. Soc., Chem. Commun. 1995, 1503-1504.
15. 8. For a review on the intramolecular Michael addition reaction, see: Jung, M. E. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I.; Paquette, L. A. Eds.; Pergamon: Tokyo, 1993, vol. 4, Chapter 1, p.24-30.
16. W = 0.088.
17. 10. Sheldrick, G.M. SHELXS-86, Program for Crystal Structure Determination, Univ. Göttingen, Germany 1986.
18. 11. Hall, S. R.; Flack, H. D.; Stewart, J. M., Xtal3.2, Program for X-Ray Crystal Structure Analysis, Universities of Western Australia, Geneva, and Maryland, 1992.