Regioselectivity of MAO-catalyzed allylmetallation of conjugated enynes with allylzirconiums

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9727-9730

  Yamanoi, Shigeo ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ALLENE DERIVATIVE; ALLYL COMPOUND; ALUMINUM DERIVATIVE; METAL DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CONJUGATION; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0032564598     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02236-9     Document Type: Article

References (32)

1. 1. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. (correction) ibid. 1997, 38, 5573. See also, Suzuki, K.; Imai, T.; Yamanoi, S.; Chino, M.; Matsumoto, T. Angew. Chem. 1997, 109, 2578; Angew. Chem., Int. Ed. Engl. 1997, 38, 2469.
2. 1. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. (correction) ibid. 1997, 38, 5573. See also, Suzuki, K.; Imai, T.; Yamanoi, S.; Chino, M.; Matsumoto, T. Angew. Chem. 1997, 109, 2578; Angew. Chem., Int. Ed. Engl. 1997, 38, 2469.
3. 1. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. (correction) ibid. 1997, 38, 5573. See also, Suzuki, K.; Imai, T.; Yamanoi, S.; Chino, M.; Matsumoto, T. Angew. Chem. 1997, 109, 2578; Angew. Chem., Int. Ed. Engl. 1997, 38, 2469.
4. 1. Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. (correction) ibid. 1997, 38, 5573. See also, Suzuki, K.; Imai, T.; Yamanoi, S.; Chino, M.; Matsumoto, T. Angew. Chem. 1997, 109, 2578; Angew. Chem., Int. Ed. Engl. 1997, 38, 2469.
5. 2. (a) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett 1993, 341.
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10. 3. Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem. 1995, 107, 1255; Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
11. 4. Courtois, G.; Mauze, B.; Miginiac, L. J. Organomet. Chem. 1974, 72, 309.
12. 5. For allylmetallation of alkynes, see: (a) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781.
13. (b) Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513.
14. (c) Okada, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1996, 118, 6076.
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16. (e) Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581.
17. (f) Negishi, E.; Takahashi, T. Synthesis 1988, 1.
18. (g) Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505. See also for alkylmetallation of alkynes: Nishimae, S.; Inoue, R.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 785.
19. (g) Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505. See also for alkylmetallation of alkynes: Nishimae, S.; Inoue, R.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 785.
20. 2Zr(H)Cl, see: Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
21. 2Zr(H)Cl, see: Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
22. 2Zr(H)Cl, see: Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
23. 3Al (2:1), Al = 6 wt% in toluene, mw = 1200, used for this reaction was kindly donated from Tosoh Akzo Co.
24. 8. When the reaction temperature was raised more slowly, the yield was lower. See ref. 1.
25. 13C NMR, IR, and high-resolution MS and/or combustion analysis.
26. 10. The geometries of the double bonds in 5, 7, and 8 were confirmed by NOE correlation.
27. 11. The silyl group was removed for facilitating the structural analysis. In the reaction of eq. 5, other two possible geometrical isomers, (6Z, SE) and (6E, 8Z), were less than 2% in the linear product (HPLC). Conversely, the (6E, 8E) and (6Z, 8Z) isomers were <2% in the linear product 12 in the case of eq. 6.
28. 12. For 1,3-metallotropic shift, see: a) Mashima, K.; Yasuda, H.; Asami, K.; Nakamura, A. Chem. Lett. 1983, 219.
29. b) Martin, H. A.; Lemaire, P. J.; Jellinek, F. J. Organomet. Chem. 1968, 14, 149.
30. c) Mann, B. E. in Comprehensive Organometatlic Chemistry, Wilkinson, G.; Gordon, F.; Stone, A.; Abel, E. W. Eds.; Pergamon: Oxford, 1982; Vol. 3, pp 89-172.
31. 13. Though formally expectable, no allene-containing products were observed.
32. 14. Note that the 1,3-shift (supra) of "Zr" to the other face of the C=C bond in I leads to ent-II, which also gives III.