MAO-catalyzed allylzirconation of 1-alkynes

Tetrahedron Letters

Volumn 38, Issue 17, 1997, Pages 3031-3034

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

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALLENE DERIVATIVE; POLYENE;

ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030891147     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00527-3     Document Type: Article

References (32)

1. For hydrozirconation of allenes, see: (a) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett 1993, 341.
2. (b) Suzuki, K.; Hasegawa, T.; Imai, T.; Maeta, H.; Ohba, S. Tetrahedron 1995, 51, 4482.
3. (c) Chino, M.; Matsumoto, T.; Suzuki, K. Synlett 1994, 359.
4. For a recent review on organozirconocene compounds in organic synthesis, see: Wipf, P.; Jahn, H. Tetrahedron 1996, 52, 12853.
5. For reviews, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
6. (b) Knochel, P. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, p 865.
7. (c) Oppolzer, W. In Comprehensive Organic Synthesis, Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, p 29.
8. (d) Normant, J.-F.; Alexakis, A. Synthesis 1981, 841.
9. (e) Negishi, E. Pure Appl. Chem. 1981, 53, 2333.
10. (a) Brintzinger, H. H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1143.
11. (b) Jordan, R. F. Adv. Organomet. Chem. 1991, 32, 325.
12. (c) Sinn, H.; Kaminsky, W. Adv. Organomet. Chem. 1980, 18, 99.
13. (d) Ziegler, K.; Holzkamp, E.; Breil, H.; Martin, H. Angew. Chem. 1955, 67, 541.
14. (e) Natta, G. Angew. Chem. 1956, 68, 3931.
15. For examples of allylmetallation of alkynes, see: (a) Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513.
16. (b) Okada, K.; Ohshima, K.; Utimoto, K. J. Am. Chem. Soc. 1996, 118, 6076.
17. (c) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519.
18. (d) Takahashi, T.; Suzuki, N.; Kageyama, M.; Kondakov, D. Y.; Hara, R. Tetrahedron Lett. 1993, 34, 4811.
19. (e) Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581.
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21. Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863. See also ref. 3e.
22. Suzuki, K. Pure Appl. Chem. 1994, 66, 1557, and the references cited therein.
23. Wipf, P.; Xu, W. J. Org. Chem. 1993, 58, 825.
24. For preparation of 1, see: Dauben, W. G.; Shapiro, G. J. Org. Chem. 1984, 49, 4252.
25. Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
26. When the temperature was raised more slowly (-78 to 25 °C during 1 h), the yield was lower (66%).
27. Ethylation product was not observed.
28. 3Al (2:1), Al = 6 wt% in toluene, mw ≈ 1200] was used throughout this study, which was kindly donated from Tosoh Akzo Co.
29. 15
30. 1H NMR and capillary GC analysis. The E/Z assignment was based on the extensive decoupling study. For silyloxydienes 3, 7, 8, 11, 12 and 14, the structures were determined for the alcohols obtained by removal of the silyl group (TBAF). equation presented
31. The reaction with a tert-alkyl-substituted alkyne (e.g., 21) was sluggish.
32. 4 (unpublished result of S. Yamanoi).