205880-27-9Relevant academic research and scientific papers
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.
Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
Brungs,Danielmeier,Jakobi,Nothhelfer,Stahl,Zietlow,Steckhan
, p. 575 - 590 (2007/10/03)
Three different electrochemical methods have been applied for the synthesis of chiral building blocks for diastereoselective amidoalkylation reactions. These are A. the direct anodic α-methoxylation of amides and carbamates; B. anodic methoxylative decarboxylation of α-amino acid derivatives (Hofer-Moest reaction) C. indirect NaCl mediated anodic α-methoxylation of α-amino acid derivatives. The application of these building blocks for the synthesis of enantiomerically pure α-amino acids, dichiral 1,2-amino alcohols and chiral 1,3-diamines is described.
