Electrogenerated chiral cationic glycine equivalents - Part 1: The 6-methoxy derivative of cyclo(L-Pro-Gly)

Article abstract of DOI:10.1016/S0040-4020(98)00081-7

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.