77642-81-0Relevant 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 (2002)
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.
Manganese-promoted regioselective ring-opening of 2,3-epoxy acid derivatives: a new route to α-hydroxy acid derivatives
Concellon, Jose M.,Bernad, Pablo L.,Rodriguez-Solla, Humberto,Diaz, Pamela
experimental part, p. 2178 - 2184 (2009/12/31)
A simple and general methodology directed towards the synthesis 3-aryl-2-hydroxy amides, or esters with total regioselectivity from the easily available 2,3-epoxy amides or esters, promoted by active manganese is described. Utilizing enantiopure epoxy amides as starting materials, the corresponding 3-aryl-2-hydroxy amides in enantiopure form are also available. Some synthetic applications of selected examples of 3-aryl-2-hydroxy carboxylic acid derivatives are shown. A mechanism has been proposed to explain this novel reaction.
Transformation of α,β-epoxyesters into 2,3-dideuterioesters promoted by samarium diiodide
Concellon, Jose M.,Bardales, Eva,Llavona, Ricardo
, p. 1585 - 1588 (2007/10/03)
An easy and general sequenced elimination/reduction process by means of samarium diiodide, in the presence of D2O, provides an efficient method for synthesizing 2,3-dideuterioesters 2. The reaction can be also carried out in the presence of H2O instead of D2O, yielding the corresponding saturated esters 4. Other deuterated esters have been also obtained. A mechanism to explain this synthesis has been proposed.
ANOMALOUS CLEAVAGE OF GLYCIDIC ACIDS
Kuroyan, R. A.,Markosyan, A. I.,Engoyan, A. P.,Vartanyan, S. A.
, p. 2219 - 2221 (2007/10/02)
The esters of 3-cyclohexyl- and 3-(2,2-dimethyl-4-tetrahydropyranyl)-2-methyl-2,3-epoxypropionic acids were obtained by the reaction of cyclohexanecarbaldehyde and 2,2-dimethyltetrahydro-4-pyrancarbaldehye with 2-chloropropionic esters.Decarboxylation of the acids corresponding to the obtained esters takes place through cleavage of the oxide ring at the C2 atom.
