31045-09-7Relevant articles and documents
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.
