B(C6F5)3-catalyzed allylation of secondary benzyl acetates with allylsilanes

Organic Letters

Volumn 3, Issue 17, 2001, Pages 2705-2707

  Rubin, Michael ^a   Gevorgyan, Vladimir ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008890383     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016300i     Document Type: Article

References (27)

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5. (c) Mayr, H.; Gorath, G.; Bauer, B. Angew. Chem., Int. Ed. Engl. 1994, 33, 788.
6. See, for example: Cella, J. A. J. Org. Chem. 1982, 47, 2125.
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9. Murakami, M.; Kato, T.; Mukaiyama, T. Chem. Lett. 1987, 1167.
10. Hayashi, M.; Inubushi, A.; Mukaiyama, T. Chem. Lett. 1987, 1975.
11. 3 as a catalyst for 1,3-isomerization of allylstannanes, see:
12. (b) Marshall, J. A.; Gill, K. J. Organomet. Chem. 2001, 624, 294. For hydrosilylation of carbonyl compounds and imines, see:
13. (c) Blackwell, J. M.; Sonmor, E. R.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921.
14. (d) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090. For allylstannylation of aldehydes, see:
15. (e) Blackwell, J. M.; Piers, W. E. Org. Lett. 2000, 2, 695. For silylation of alcohols, see:
16. (f) Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem. 1999, 64, 4887.
17. (a) Gevorgyan, V.; Liu, J.-X.; Rubin, M.; Benson, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 8918.
18. (b) Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179.
19. Gevorgyan, V.; Rubin, M.; Liu, J.-X.; Yamamoto. Y. J. Org. Chem. 2001, 66, 1672.
20. 1H NMR analyses of the crude reaction mixtures.
21. Bergquist, C.; Bridgewater, B. M.; Harlan, C. J.; Norton, J. R.; Friesner, R. A.; Perkin, G. J. Am. Chem. Soc. 2000, 122, 10581.
22. 3, preliminarily exposed to wet air, led to the formation of notable amounts of alkenes.
23. 3 were sluggish and incomplete.
24. 2 (1 mL) was added 3f (1 mmol, 164 mg), followed by the addition of allyltrimethylsilane (1.5 mmol, 240 μL). The mixture was stirred at room temperature, and the reaction course was monitored by capillary GLC analysis. After the reaction was complete (12 h for 4a), the mixture was filtered through a short column (silica gel) and concentrated. Purification by column chromatography (silica gel, hexane as an eluent) gave 133 mg (91%) of 4a.
25. Reactions, in these cases, were finished in 5-6 h, whereas normally the reaction needed 12-48 h for completion.
26. 3 did not exeed 20%.
27. 3 with alcohols and nitriles see ref 12.