139244-10-3Relevant academic research and scientific papers
Domino carbopalladation-carbonylation: Investigation of substrate scope
Seashore-Ludlow, Brinton,Danielsson, Jakob,Somfai, Peter
, p. 205 - 216 (2012/03/27)
This work gives an in depth account of our domino carbopalladation- carbonylation method for substrates possessing β-hydrogens. The scope of the method is examined for allylic amines containing trisubstituted olefins and we detail our attempts toward the diastereospecific synthesis of contiguous quaternary centers using this technology. The results give key insights into the relative rates of the competing reactions of the alkyl palladium intermediates, which is crucial for the understanding and development of new domino processes.
Synthesis of (E)-α,β-unsaturated esters with total or high diastereoselectivity from α,β-epoxyesters
Concellon, Jose M.,Bardales, Eva
, p. 189 - 191 (2007/10/03)
Chemical equation presented High stereoselective β-elimination in 2,3-epoxyesters 1 was achieved using samarium diiodide, yielding α,β-unsaturated esters 2, in which the C=C bond is di-, tri- or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the corresponding lithium enolates of a-chloroesters with aldehydes or ketones at -78 °C. The influence of the reaction conditions and the structure of the starting compounds in the stereoselectivity of the β-elimination reaction is also discussed.
