205875-06-5Relevant articles and documents
Electrogenerated chiral cationic glycine equivalents - Part 1: The 6-methoxy derivative of cyclo(L-Pro-Gly)
Kardassis, Georgios,Brungs, Peter,Steckhan, Eberhard
, p. 3471 - 3478 (2007/10/03)
The cyclic N,O-acetal cyclo(L-Pro-Gly(OMe)OMe (8) has proved to be an effective chiral electrophilic glycine equivalent which is applicable in nucleophilic substitution reactions not only under Broenstedt acid catalysis but also under Lewis acid catalysis with excellent diastereoselectivities. This chiral building block can easily be obtained by electrochemical methoxylative decarboxylation of the cyclic dipeptide 6 generated from L-proline and aminomalonic diester. Thus, enantiomerically pure D-allyl glycine has been generated.
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.