Preparation of silyl enol ethers from acyloin derivatives using silyllithium reagents

Tetrahedron Letters

Volumn 49, Issue 13, 2008, Pages 2088-2090

  Robertson, Bradley D ^a   Hartel, Aaron M ^a  

^a WINTHROP UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLOIN DERIVATIVE; ALDEHYDE DERIVATIVE; DIMETHYLPHENYLSILYLLITHIUM; ETHER DERIVATIVE; LITHIUM DERIVATIVE; METHYLDIPHENYLSILYLLITHIUM; ORGANIC COMPOUND; SILYL ENOL ETHER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 39649120531     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.01.133     Document Type: Article

References (31)

1. Brownbridge P. Synthesis (1983) 1-28
2. Brownbridge P. Synthesis (1983) 85-104
3. Mukaiyama T. Pure Appl. Chem. 55 (1983) 1749-1758
4. Ohmura T., Yamamoto Y., and Miyaura N. Organometallics 18 (1999) 413-416
5. Still W.C., and Macdonald T.L. J. Am. Chem. Soc. 96 (1974) 5561-5563
6. Brook A.G., MacRae D.M., and Limburg W.W. J. Am. Chem. Soc. 89 (1967) 5493-5495
7. Larson G.L., Berrios R., and Prieto J.A. Tetrahedron Lett. 30 (1989) 283-286
8. Hudrlik P.F., Misra R.N., Withers G.P., Hudrlik A.M., Rona R.J., and Arcoleo J.P. Tetrahedron Lett. 18 (1976) 1453-1456
9. Hudrlik P.F., Wan C.-N., and Withers G.P. Tetrahedron Lett. 18 (1976) 1449-1452
10. Bassindale A.R., Brook A.G., Chen P., and Lennon J. J. Organomet. Chem. 94 (1975) C21-C25
11. Komatsu M., Jinil C., Imai E., Oderaotoshi Y., and Minakata S. Tetrahedron Lett. 42 (2001) 9221-9223
12. Kato M., Mori A., Oshino H., Enda J., Kobayashi K., and Kuwajima I. J. Am. Chem. Soc. 106 (1984) 1773-1778
13. Hudrlik P.F., Schwartz R.H., and Kulkarni A.K. Tetrahedron Lett. 24 (1979) 2233-2236
14. Hudrlik P.F., Hudrlik A.M., and Kulkarni A.K. J. Am. Chem. Soc. 107 (1985) 4260-4264
15. Takeda K., Kawanishi E., Sasaki M., Takahashi Y., and Yamaguchi K. Org. Lett. 4 (2002) 1511-1514
16. Sasaki M., Kawanishi E., Nakai Y., Matsumoto T., Yamaguchi K., and Takeda K. J. Org. Chem. 68 (2003) 9330-9339
17. Tanaka K., Masu H., Yamaguchi K., and Takeda K. Tetrahedron Lett. 46 (2005) 6429-6432
18. Okugawa S., Masu H., Yamaguchi K., and Takeda K. J. Org. Chem. 70 (2005) 10515-10523
19. Sasaki M., Horai M., and Takeda K. Tetrahedron Lett. 47 (2006) 9271-9273
20. Brook A.G., and Fieldhouse S.A. J. Organomet. Chem. 10 (1967) 235-246
21. Nakajima T., Segi M., Sugimoto F., Hioki R., Yokota S., and Miyashita K. Tetrahedron 49 (1993) 8343-8358
22. Aggarwal V.K., Sheldon C.G., Macdonald G.J., and Martin W.P. J. Am. Chem. Soc. 124 (2002) 10300-10301
23. Brook A.G., Limburg W.W., MacRae D.M., and Fieldhouse S.A. J. Am. Chem. Soc. 89 (1967) 704-706
24. Takeda K., Ubayama H., Sano A., Yoshii E., and Koizumi T. Tetrahedron Lett. 39 (1998) 5234-5246
25. Reich H.J., Rusek J.J., and Olsen R.E. J. Am. Chem. Soc. 101 (1979) 2225-2227
26. Reich H.J., Holtan R.C., and Borkowsky S.L. J. Org. Chem. 52 (1987) 312-314
27. Reich H.J., Holtan R.C., and Bolm C. J. Am. Chem. Soc. 112 (1990) 5609-5617
28. Fleming I., Roberts R.S., and Smith S.C. J. Chem. Soc., Perkin Trans. 1 (1998) 1215-1228
29. Reynolds S.C., Wengryniuk S.E., and Hartel A.M. Tetrahedron Lett. 48 (2007) 6751-6753
30. Moser W.H. Tetrahedron 57 (2001) 2065-2084
31. Reaction times longer than 15 min often resulted in significant formation of the α-reduced ketone.