343360-95-2Relevant academic research and scientific papers
Organozinc alkoxide-promoted aldol-Tishchenko reaction of aliphatic aldehydes: An expedient entry to prepare the α-methylene ketones
Hon, Yung-Son,Chang, Chun-Ping
, p. 5267 - 5275 (2005)
i-PrOZnEt is an excellent reagent to promote the aldol-Tishchenko reaction of the aliphatic aldehydes tethered with other labile functional groups. The 1,3-diol monoesters 4 were formed as the major products, which could be converted to α-methylene ketone
Rapid organocatalytic aldehyde-aldehyde condensation reactions
Erkkilae, Anniina,Pihko, Petri M.
, p. 4205 - 4216 (2008/03/14)
We report the results of the systematic optimization of the α-methylenation of aldehydes with aqueous formaldehyde. A simple combination of a secondary amine catalyst and a weak acid co-catalyst has been identified, allowing access to α-substituted acroleins in a matter of minutes. In the absence of formaldehyde, the catalytic system promoted the self-condensation reaction of α,β-unsaturated aldehydes. Both of these reactions exhibited linear relationships between co-catalyst acidities and reaction rates. A second-order dependence of catalyst concentration was observed, pointing to the involvement of two molecules of the ammonium catalyst in the rate-determining step. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
TiF4-mediated biomimetic alkylation-cyclization cascade reaction of 2-trimethylsilylmethyl-1,5-dienes with aldehydes
Anastasia, Luigi,Giannini, Elios,Zanoni, Giuseppe,Vidari, Giovanni
, p. 5803 - 5806 (2007/10/03)
TiF4 has proven to be the Lewis acid of choice for promoting the biomimetic addition of 2-trimethylsilylmethyl-1,5-dienes to aliphatic aldehydes with concomitant cyclization. 1,3-cis-Disubstituted methylenecyclohexanes are thus produced in good yields and high diastereoselectivity. The reaction appears to proceed via a highly concerted mechanism involving a chair-like transition state.
