70841-77-9Relevant academic research and scientific papers
Enantioselective decarboxylation-reprotonation of an α-amino malonate derivative as a route to optically enriched cyclic α-amino acid
Rogers, Louis M.-A.,Rouden, Jacques,Lecomte, Ludovic,Lasne, Marie-Claire
, p. 3047 - 3050 (2003)
Chiral tertiary amines have been examined as enantioselective decarboxylation-reprotonation reagents for the synthesis of α-amino acids via α-aminomalonates. N-Acetyl pipecolic acid ethyl ester, as a model compound, was obtained in good yield and 52% enantiomeric excess using a quinidine derived base.
Concurrent esterification and N-acetylation of amino acids with orthoesters: A useful reaction with interesting mechanistic implications
Gibson, Sarah,Romero, Dickie,Jacobs, Hollie K.,Gopalan, Aravamudan S.
scheme or table, p. 6737 - 6740 (2011/02/25)
The concurrent esterification and N-acetylation of amino acids has been studied with triethyl orthoacetate (TEOA) and triethyl orthoformate (TEOF). In a surprising finding, only 1 equiv of TEOA in refluxing toluene was necessary to convert l-proline and l-phenylalanine into the corresponding N-acetyl ethyl esters in good yield. The same transformation using TEOF was not effective. Stereochemical outcome and stoichiometric studies as well as structural variation of the amino acids in this reaction provided unexpected mechanistic insight.
