36576-19-9Relevant academic research and scientific papers
Tetramic Acid Chemistry. Part 1. Reinvestigation of Racemisation during the Synthesis of Tetramic Acids via Dieckmann Cyclisation
Poncet, Joel,Jouin, Patrick,Castro, Bertrand,Nicolas, Louisette,Boutar, Mohamed,Gaudemer, Alain
, p. 611 - 616 (2007/10/02)
Epimerisation during the synthesis of tetramic acids by Dieckmann cyclisation of the corresponding chiral N-acyl-α-amino esters was investigated.In the case of the isoleucine derivative, the extent of epimerisation was directly evaluated by 1H NMR analysis of the 3-acylated tetramic acids (3a,b) and (5a).A chemical correlation was carried out in the case of the 5-benzyl derivative (8h).The moderate overall yield and the partial epimerisation at position C-5 limit the usefulness of this approach for tetramic acid preparation.
