TY - JOUR
TI - Improvement on the synthesis of (E)-alk-3-enoic acids
AU - Ragoussis, N.
AU - Ragoussis, V.
JO - Journal of the Chemical Society, Perkin Transactions 1
PY - 1998
VL - null
TODO - 21
SP - 3529-3533
PB - Royal Society of Chemistry
SN - 0300-922X, 1364-5463
TODO - 10.1039/a806173d
TODO - null
TODO - (E)-Alk-3-enoic acids have been prepared in high yield (85-90%) and excellent stereoselectivity (98-99%) by a modified Knoevenagel condensation of a straight carbon chain aldehyde with malonic acid, in dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) at 100°C, in the presence of piperidinium acetate as catalyst. Condensation of the aldehyde with a monoester of malonic acid, under the above conditions, gave the corresponding ester of (E)-alk-3-enoic acid in high yield (76-82%) and good stereoselectivity (90-92%). Condensation of the aldehyde with cyanoacetic acid gave the β,γ-unsaturated nitrile in moderate yield (35-40%) without stereoselectivity.
ER -