Group-selective hydroalumination: A novel route to stereogenic tert-alcohol centers

Organic Letters

Volumn 3, Issue 7, 2001, Pages 1057-1060

  Ohmori, Ken ^a   Suzuki, Takao ^a   Taya, Kimiko ^a   Tanabe, Daisuke ^a   Ohta, Toshihiro ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

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EID: 0008210090     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0156704     Document Type: Article

References (30)

1. For selected examples of group-selective reactions, see: (a) Curran, D. P.; Qi, H.; DeMello, N. C.; Lin, C.-H. J. Am. Chem. Soc. 1994, 116, 8430-8431.
2. (b) Curran, D. P.; Geib, S. J.; Lin, C.-H. Tetrahedron: Asymmetry 1994, 5, 199-202.
3. (c) Wipf, P.; Kim, Y. Tetrahedron Lett. 1992, 33, 5477-5480.
4. (d) Harada, T.; Wada, I.; Uchimura, J.; Inoue, A.; Tanaka, S.; Oku, A. Tetrahedron Lett. 1991, 32, 1219-1222
5. (e) Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525-1529.
6. (f) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 503-5305.
7. (g) Waldmann, H. Organic Synthesis Highlights II; VCH: New York; pp 203-222, and the references therein.
8. Nagasawa, T.; Taya, K.; Kitamura, M.; Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949-8950.
9. Easily prepared from the corresponding ester derivative by treatment with 2.5 equiv of alkynyllithium.
10. For the hydroalumination reaction of propargyl alcohols, see: (a) Attenburrow, J.; Cameron, A. F. B.; Chapman, J. H.; Evans, R. M.; Hems, B. A,; Jansen, A. B. A.; Walker, T. J. Chem. Soc. 1952, 1094-1111.
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12. (c) Corey, E. J.; Katzenellenbogen, J. A.; Posner, G. A. J. Am. Chem. Soc. 1967, 89, 4245-4247.
13. (d) Corey, E. J.; Katzenellenbogen, J. A.; Gilman, N. W.; Roman, S. A.; Erickson, B. W. J. Am. Chem. Soc. 1968, 90, 5618-5620.
14. (e) Corey, E. J.; Kirst, H. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1970, 92, 6314-6319.
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16. (g) Rollinson, S. W.; Amos, R. A.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1981, 103, 4114-4125.
17. (h) Denmark, S. E.; Jones. T. K. J. Org. Chem. 1982, 47, 4595-4597. For the mechanism of hydroalumination, see:
18. (i) Franzus, B.; Snyder, E. I. J. Am. Chem. Soc. 1965, 87, 3423-3429.
19. (j) Snyder, E. I. J. Org. Chem. 1967, 32, 3531-3534.
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21. (l) Grant, B.; Djerassi, C. J. Org. Chem. 1974, 39, 968-970.
22. (m) Kakinuma, K.; Matsuzawa, T.; Eguchi, T. Tetrahedron 1991, 47, 6975-6982.
23. For a review of the hydroalumination reaction, see: Zweifel, G; Miller, J. A. Org. React. 1984, 32, 375-517.
24. 2, hexane/EtOAc = 80/20) to give 5 (131 mg, 80%, 5a/5b = 88/12) as colorless oil.
25. All new compounds were fully characterised by spectroscopic means and combustion analysis. The diastereomer ratios of the products were determined by NMR (400 MHz) analysis. Stereochemical assignments were based on extensive correlation studies.
26. 2, hexane/EtOAc = 85/15) to afford 9b (948 mg, 94%) as a colorless oil.
27. Marshall, J. A.; Garofalo, A. W.; Sedrani, R. C. Synlett 1992, 643-645.
28. Santini, C.; Ball, R. G.; Berger, G. D. J. Org. Chem. 1994, 59, 2261-2266, and references therein.
29. Recently, a report has appeared on the total synthesis of zaragozic acid A which employs a related hydroalumination reaction. However, different alkynyl groups were used, and the mechanism for the selection is different (personal communication from Dr. Tomooka): Tomooka, K; Kikuchi, M.; Igawa, K.; Suzuki, M.; Keong, P-.H.; Nakai, T. Angew. Chem., Int. Ed. 2000, 39, 4502-4505.
30. Itazaki, H.; Nagashima, K.; Kawamura, Y.; Matsumoto, K.; Nakai, H.; Terui, Y. J. Antibiot. 1992, 45, 38-49.