205880-24-6Relevant articles and documents
Electrogenerated chiral cationic glycine equivalents - Part 2: Chiral 3-methoxy-2,5-morpholinediones from (S)-α-hydroxy acids and dimethyl aminomalonate
Kardassis, Georgios,Brungs, Peter,Nothhelfer, Christoph,Steckhan, Eberhard
, p. 3479 - 3488 (2007/10/03)
Chiral 3-methoxy-2,5-morpholinediones which are cyclic N,O-acetals have proved to be excellent chiral cationic amino acid equivalents, especially if larger nucleophiles are employed. They are easily obtained from dipeptolides formed between chiral α-hydroxy acids and dimethyl amino malonate via regioselective electrochemical methoxylation followed by intramolecular lactonizatian after decarboxylation. The lactonization can be performed quantitatively from the open-chain peptolide by condenzation under reduced pressure at elevated temperature. The easy separation of the desired amino acid and the α-hydroxy acid being the chiral auxiliary by extraction is valuable.