Enzymatic alkylation of α-cyanoketones by bakers yeast

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5121-5124

  Smallridge, Andrew J ^a   Ten, Abilio ^a   Trewhella, Maurie A ^a  

^a VICTORIA UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; CYANIC ACID DERIVATIVE; CYANOKETONE; NITRILE; ORGANIC SOLVENT;

ALKYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; ENANTIOMER; ENZYME MECHANISM; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

SACCHAROMYCES CEREVISIAE;

EID: 0032500069     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00945-9     Document Type: Article

References (9)

1. 1. Csuk, R., Glänzer, B. I., Chem. Rev. 1991, 91, 49.
2. 2. Servi, S., Synthesis, 1990, 1.
3. 3. Medson, C., Smallridge, A. J., Trewhella, M. A., Tetrahedron: Asymmetry, 1997, 8, 1049 and references cited therin.
4. 4. The α-cyanoketones were prepared using the procedure of Dorsch, J., and McElvain, S. M., J. Am. Chem. Soc., 1932, 54, 2960.
5. 5. Itoh, T., Takagi, Y., and Fujisawa, T., Tetrahedron Letters, 1989, 30, 3811.
6. 6. Fuganti, C., Pedrocchi-Fantoni, G., Servi, S., Tetrahedron Letters, 1990, 31, 4195.
7. 3), 7.72, (1H, q, J 7.2 Hz, H3).
8. 8. These results are in full agreement with a previous publication which showed that under conventional Knoevenagel reaction conditions, the reaction of ethyl cyanoacetate (13) with acetaldehyde using piperidine/acetic acid as the catalyst gave ethyl (E)-2-cyanobut-2-enoate (17) exclusively, Yamamoto, Y. and Nishii, S., J. Org. Chem., 1988, 53, 3597.
9. 9. Popp, F. D., and Catala, A., J. Org. Chem., 1961, 26, 2738.