Lithium Acetate Catalyzed Aldol Reaction between Aldehyde and Trimethylsilyl Enolate in a Dimethylformamide-H2O Solvent

Chemistry Letters

Volumn 32, Issue 8, 2003, Pages 696-697

  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

ALCOHOL DERIVATIVE; ALDEHYDE; ESTER; LITHIUM ACETATE; N,N DIMETHYLFORMAMIDE; SOLVENT; TRIMETHYLSILYL DERIVATIVE; TRIMETHYLSILYL ENOLATE; UNCLASSIFIED DRUG; WATER;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST;

EID: 0242720576     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2003.696     Document Type: Article

References (17)

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13. Other systems: a) A. Lubineau, J. Org. Chem., 51, 2142 (1986). b) T.-P. Loh, L.-C. Feng, and L.-L. Wei, Tetrahedron, 56, 7309 (2000). c) M. Ohkouchi, M. Yamaguchi, and T. Yamagishi, Enantiomer, 5, 71 (2000). d) M. Ohkouchi, D. Masui, M. Yamaguchi, and T. Yamagishi, J. Mol. Catal. A: Chem., 170, 1 (2001). e) M. Ohkouchi, D. Masui, M. Yamaguchi, and T. Yamagishi, Nippon Kagaku Kaishi, 2002, 223.
14. Other systems: a) A. Lubineau, J. Org. Chem., 51, 2142 (1986). b) T.-P. Loh, L.-C. Feng, and L.-L. Wei, Tetrahedron, 56, 7309 (2000). c) M. Ohkouchi, M. Yamaguchi, and T. Yamagishi, Enantiomer, 5, 71 (2000). d) M. Ohkouchi, D. Masui, M. Yamaguchi, and T. Yamagishi, J. Mol. Catal. A: Chem., 170, 1 (2001). e) M. Ohkouchi, D. Masui, M. Yamaguchi, and T. Yamagishi, Nippon Kagaku Kaishi, 2002, 223.
15. Other systems: a) A. Lubineau, J. Org. Chem., 51, 2142 (1986). b) T.-P. Loh, L.-C. Feng, and L.-L. Wei, Tetrahedron, 56, 7309 (2000). c) M. Ohkouchi, M. Yamaguchi, and T. Yamagishi, Enantiomer, 5, 71 (2000). d) M. Ohkouchi, D. Masui, M. Yamaguchi, and T. Yamagishi, J. Mol. Catal. A: Chem., 170, 1 (2001). e) M. Ohkouchi, D. Masui, M. Yamaguchi, and T. Yamagishi, Nippon Kagaku Kaishi, 2002, 223.
16. 2O and 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 (98.3 mg, 97%) as a white powder.
17. Although a small amount of acetal 2, a co-product, was obtained under the nonaqueous condition, it was easily converted to normal aldol and starting aldehyde on treatment with 1 N HCl.