Intramolecular proton transfer

Organic Letters

Volumn 4, Issue 15, 2002, Pages 2593-2595

  Zimmerman, Howard E ^a   Wang, Pengfei ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012144938     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026251p     Document Type: Article

References (17)

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3. (b) Zimmerman, H. E.; Linder, L. W. J. Org. Chem. 1985, 48, 1637-1646.
4. Zimmerman, H. E.; Ignatchenko, A. J. Org. Chem. 1999, 64, 6635-6645.
5. (a) A 15-step synthesis was employed to obtain the silyl enol ethers and will be described in our full publication. (b) In a typical run, 4.0 mg of the silyl enol ether in 0.40 mL of acetonitrile was treated with 2 equiv of acetic acid and 2 equiv of tetrabutylammonium fluoride (1.0 M in THF). After 4 h, the reaction was 90% complete, and the ketonized diastereomers were analyzed by proton NMR.
6. (a) Smirnov, S. N.; Golubev, N. S.; Denisov, G. S., Bendict, H.; Schah-Mohammdei, P.; Limbach, H.-H. J. Am. Chem. Soc. 1996, 118, 4094-4101.
7. (b) Golubev, N. S.; Smirnov, S. N., Gindin, V. A.; Denisov, G. S.; Benedict, H.; Limbach, H.-H. J. Am. Chem. Soc. 1994, 116, 12055-12056.
8. (a) Base-Catalyzed Rearrangements. In Molecular Rearrangements; Zimmerman, H. E., Ed.; P. DeMayo, Interscience: New York, 1963; Chapter 6, pp 345-406.
9. (b) Malhotra, S. K.; Ringold, H. J. J. Am. Chem. Soc. 1965, 87, 3228-3236;
10. 8 and it seems that the rediscoveries are often cited.
11. (a) Gerlach, U.; Haubenreich, T.; Hünig, S.; Keita, Y. Chem. Ber. 1993, 126, 1205-1215.
12. (b) Takano, S.; Kudo, J.; Takahashi, N.; Ogasawara, K. Tetrahedron Lett. 1986, 2405-2408.
13. (c) Takano, S.; Uchida, W.; Hatakeyama, S.; Ogaswara, K. Chem. Lett. 1982, 733-737.
14. (d) Takano, S.; Goto, E.; Ogasawara, K. Tetrahedron Lett. 1982, 5567-5569.
15. (e) Takano, S.; Yamada, S.; Numata, H.; Hatakeyama, S.; Ogasawara, K. Heterocycles 1983, 20, 2159-2162.
16. (f) Takano, S.; Tananka, M.; Seo, M.; Hirama, M.; Ogasawara, K. J. Org. Chem. 1985, 50, 931-936.
17. (g) Note also: Hünig, S. Protonation of Carbanions and Polar Double Bonds. Houben-Weyl, Methods of Organic Chemistry; G. Thieme: Stuttgart, 1996; Vol. E21D 7, pp 3851-3911.