Lithium acetate-catalyzed aldol reaction between aldehyde and trimethylsilyl enolate

Chemistry Letters

Volumn 32, Issue 5, 2003, Pages 462-463

  Nakagawa, Takashi ^a,b   Fujisawa, Hidehiko ^a,b   Mukaiyama, Teruaki ^a,b  

^a KITASATO INSTITUTE   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BASE; LITHIUM ACETATE; PYRIDINE DERIVATIVE; SILANE DERIVATIVE; SOLVENT; TRIMETHYLSILYL ENOLATE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE;

EID: 0042266245     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.462     Document Type: Article

References (10)

1. H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 182; H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 858; T. Mukaiyama, H. Fujisawa, and T. Nakagawa, Helv. Chim. Acta, 85, 4518 (2002).
2. H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 182; H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 858; T. Mukaiyama, H. Fujisawa, and T. Nakagawa, Helv. Chim. Acta, 85, 4518 (2002).
3. H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 182; H. Fujisawa and T. Mukaiyama, Chem. Lett., 2002, 858; T. Mukaiyama, H. Fujisawa, and T. Nakagawa, Helv. Chim. Acta, 85, 4518 (2002).
4. T. Mukaiyama, T. Nakagawa, and H. Fujisawa, Chem. Lett., 32, 56 (2003).
5. F. G. Bordwell, Acc. Chem. Res., 21, 456 (1988); F. G. Bordwell, J. C. Branca, D. L. Hughes, and W. N. Olmstead, J. Org. Chem., 45, 3305 (1980).
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7. Although a small amount of acetal 2 was co-produced, it was easily converted to normal aldol and starting aldehyde on treatment with 1 N HCl. See: a) E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama, and R. Noyori, J. Org. Chem., 48, 932 (1983). b) S. Matsukawa, N. Okano, and T. Imamoto, Tetrahedron Lett., 41, 103 (2000).
8. Although a small amount of acetal 2 was co-produced, it was easily converted to normal aldol and starting aldehyde on treatment with 1 N HCl. See: a) E. Nakamura, M. Shimizu, I. Kuwajima, J. Sakata, K. Yokoyama, and R. Noyori, J. Org. Chem., 48, 932 (1983). b) S. Matsukawa, N. Okano, and T. Imamoto, Tetrahedron Lett., 41, 103 (2000).
9. 2O. Organic layer was washed with brine and dried over anhydrous sodium sulfate. After filtration and evaporation of the solvent, the crude product was purified by preparative TLC to give the corresponding aldol (89.6 mg, 94%) as a white powder.
10. Y. Génisson and L. Gorrichon, Tetrahedron Lett., 41, 4881 (2000).