122798-53-2Relevant academic research and scientific papers
New synthesis of (±)-sitophilate using carboxylic acid dianion methodology - A stereoselectivity study
Gil, Salvador,Parra, Margarita,Rodriguez, Pablo,Sotoca, Enrique
, p. 3451 - 3455 (2007/10/03)
A simple two-step synthesis of (±)-sitophilate in has been developed by addition of propanal to the lithium enediolate of propanoic acid and subsequent esterification with 3-pentanol under standard Fischer conditions. Efforts to control the diastereoselectiv-ity to generate the syn isomer are described. A modest degree of asymmetric induction is found using chiral amides as base. Georg Thieme Verlag Stuttgart.
Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis-Hillman adducts. Total synthesis of (±)-sitophilate
Mateus, Cristiano R,Feltrin, Melissa P,Costa, Ana M,Coelho, Fernando,Almeida, Wanda P
, p. 6901 - 6908 (2007/10/03)
We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes.
STEREOCHEMICALLY CONTROLLED SYNTHESIS OF RACEMIC SITOPHILATE, THE AGGREGATIONAL PHEROMONE OF THE GRAIN WEEVIL
Cheskis, B. A.,Moiseenkov, A. M.,Shpiro, N. A.,Stashina, G. A.,Zhulin, V. M.
, p. 716 - 720 (2007/10/02)
Controlled condensation of propionaldehyde with Li- or Si-enolates, generated from sec-amyl propionate, readily afforded a mixture of diastereomeric 2-methyl-3-hydroxypentanoic acid 3-pentyl esters, which were easily separated by chromatography.The erythr
THE CHEMICAL IDENTIFICATION OF THE GRANARY WEEVIL AGGREGATION PHEROMONE
Phillips, Joel K.,Miller, Stephen P. F.,Andersen, John F.,Fales, Henry M.,Burkholder, Wendell E.
, p. 6145 - 6146 (2007/10/02)
(R*,S*)-1-Ethylpropyl 2-methyl-3-hydroxypentanoate is identified as the major component of the aggregation pheromone of Sitophilus granarius (L.), the granary weevil.
