368425-56-3Relevant academic research and scientific papers
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
body text, 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.
Synthesis of aliphatic (E)-α,β-unsaturated amides with high diastereoselectivity from α,β-epoxyamides promoted by SmI 2/HMPA
Concellon, Jose M.,Bardales, Eva
, p. 1523 - 1526 (2007/10/03)
Synthesis of aliphatic (E)-α,β-unsaturated amides 2, in which the C=C bond is di- or trisubstituted, is achieved by using samarium diiodide and HMPA. The starting compounds 1 were easily prepared by the reaction of the corresponding lithium or potassium e
Sequenced elimination-reduction and elimination-cyclopropanation reactions of 2,3-epoxyamides promoted by samarium diiodide. Synthesis of 2,3-dideuterioamides and cyclopropanamides
Concellón, José M.,Huerta, Mónica,Bardales, Eva
, p. 10059 - 10065 (2007/10/03)
An easy and general sequenced elimination/reduction or elimination/ cyclopropanation process promoted by samarium diiodide or/and CH 2I2/Sm provide an efficient method for synthesising 2,3-dideuterioamides 3 or cyclopropanamides 8, respectively. The transformations take place in high yields and with total or high selectivity from the easily available 2,3-epoxyamides. Graphical Abstract
Synthesis of (E)-α,β-unsaturated amides with high selectivity by using samarium diiodide
Concellon, Jose M.,Perez-Andres, Juan A.,Rodriguez-Solla, Humberto
, p. 3062 - 3068 (2007/10/03)
Stereoselective β-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield α,β-unsaturated amides 2, in which the C=C bond is di- tri-, or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the c
