17463-01-3Relevant articles and documents
A practical, efficient, and atom economic alternative to the Wittig and Horner-Wadsworth-Emmons reactions for the synthesis of (E)-α,β- unsaturated esters from aldehydes
List, Benjamin,Doehring, Arno,Hechavarria Fonseca, Maria T.,Job, Andreas,Rios Torres, Ramon
, p. 476 - 482 (2007/10/03)
We describe a highly efficient new methodology for the synthesis of (E)-α,β-unsaturated esters from aldehydes. In our DMAP-catalyzed reaction, both aromatic as well as aliphatic aldehydes furnish the desired products highly regio- and stereoselectively if treated with commercially available or synthetically easily accessible malonic acid half ester. A large scale application in the synthesis of p-methoxycinnamates, which are of use as sunscreen ingredients, is described.
TMSCl-mediated catalytic carbocupration of alkynoates: An unprecedented and remarkable effect of catalyst loading on highly selective stereochemical induction via a TMS-allenoate intermediate
Jennings, Michael P.,Sawant, Kailas B.
, p. 3201 - 3204 (2007/10/03)
The TMSCl-mediated catalytic carbocupration of alkynoates has been investigated. It has been shown that catalyst loadings as low as 30 mol% readily allow for high yields and diastereoselectivities for a series of Grignard reagents. In addition, an unprecedented and remarkable effect of catalyst loading on stereochemical induction has been observed. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
The Horner-Wadsworth-Emmons Modification of the Wittig Reaction Using Triethylamine and Lithium or Magnesium Salts
Rathke, Michael W.,Nowak, Michael
, p. 2624 - 2626 (2007/10/02)
A variety of aldehydes were converted into the corresponding α,β-unsaturated esters using triethyl phosphonoacetate and triethylamine in the presence of lithium or magnesium halides.Under the same conditions, simple methyl ketones were unreactive.