Stereoselective synthesis of stable isotope-labeled L-α-amino acids: Enantioselective synthesis of 13C-, 15N-labeled L-proline using Oppolzer's glycine template

Article abstract of DOI:10.1002/(SICI)1099-1344(1998110)41:11<983::AID-JLCR152>3.0.CO;2-M

We have developed a stereoselective route to the synthesis of stable isotope-labeled L-proline. Alkylation of (2R)-N-{N'-[bis(methylthio)methylidine]glycyl}bornane-10,2-sultam with 3-chloro-iodopropane yielded (2R)-N-{(2'S)-2'-{[Bis(methylthio)methylidine]amino}5-chloropentan-1 -oyl}bornane-10,2-sultam. Cyclization to the imino acid occurred during the sequential removal of the α-amino protecting group and the chiral auxiliary.