Fluoride-Mediated Reactions of Enol Silyl Ethers. Regiospecific Monoalkylation of Ketones

Journal of the American Chemical Society

Volumn 104, Issue 4, 1982, Pages 1025-1030

  Kuwajima, Isao ^a   Nakamura, Eiichi ^a   Shimizu, Makoto ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000141607     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00368a018     Document Type: Article

References (44)

1. Cf. House, H. O. “Modern Synthetic Reactions”; W. A. Benjamin: Menlo Park, CA, 1972; Chapter 9.
2. Cf. D'Angelo, Tetrahedron 1976, 32, 2979.
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4. Stork, G.; Hudrlik, P. F. J. Am. Chem. Soc. 1968, 90, 4462, 4464.
5. Review: Rasmussen, J. K. Synthesis 1977, 91.
6. For instance: House, H. O.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1971, 36, 2361.
7. Gall, M.; House, H. O. Org. Synth. 1972, 52, 39.
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15. Review: Jackmam, L. M.; Lange, B. C. Tetrahedron 1977, 33, 2737.
16. Preparation and reactions of “naked” enolate anions of active methylene compounds: Brandström, A.; Gustvii, K. Acta Chem. Scand. 1969, 23, 1215.
17. Noyori convincingly showed the formation of a “naked” enolate anion in such a metathesis by replacing the ammonium cation with a more stable sulfonium cation: Noyori, R.; Nishida, I.; Sakata, J.; Nishizawa, M. J. Am. Chem. Soc. 1980, 102, 1223.
18. Alkylation of the enolate generated in situ: Noyori, R.; Nishida, I.; Sakata, J. Tetrahedron Lett. 1980, 2085.
19. Aldol reaction: Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106.
20. For the use of fluoride anion for the protonolysis of silyl ethers: Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 2549.
21. For the preliminary communication, Kuwajima, I.; Nakamura, E. J. Am. Chem. Soc. 1975, 97, 3257.
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23. For instance: Nakamura, E.; Murofushi, T.; Shimizu, M.; Kuwajima, I. J. Am. Chem. Soc. 1976, 98, 2346.
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31. Patterson, J. W.; Fried, J. H. J. Org. Chem. 1974, 39, 2506.
32. Since the cleavage of Si-O bond by fluoride anion is very fast (cf. ref 14b), this result probably reflects the reactivities of the two regioisomers of the ammonium enolates: cf. Caine, D.; Huff, B. J. L. Tetrahedron Lett. 1966, 4695.
33. Johnson, F. Chem. Rev. 1968, 68, 375.
34. Cf. Kuwajima, I.; Murofushi, T.; Nakamura, E. Synthesis 1976, 602.
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39. Distinctive axial attack of reagents onto related cyclohexene derivatives. Lithio hydrazone and related species Corey, E. J.; Enders, D. Tetrahedron Lett. 1976, 3.
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41. π-Allyl palladium complex: Trost, B. M.; Strege, P. E. J. Am. Chem. Soc. 1975, 97, 2534.
42. The scope of the alkylation reaction of lithium enolates in liquid ammonia has been to a highly practical level; broadened recently Binkley, E. S.; Heathcock, C. H. J. Org. Chem. 1975, 40, 2156.
43. See also ref 18b. Cf. Stork, G.; Rosen, P.; Goldman, N.; Coombs, R. V.; Tsuji, J. J. Am. Chem. Soc. 1965, 87, 275.
44. Rathke, M. W.; Lindert, A. Synth. Commun. 1978, 8, 9.