Stereoselective synthesis of (2S,3S,4R,5S)-proline-3,4,5-d3

Article abstract of DOI:10.1016/S0040-4039(97)01189-1

A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCl₂(PPh₃)₃ followed by RuO₄-oxidation gave a 3,4-dideuterated L-pyroglutamic acid derivative which is considered to be a promising precursor for various deuterated amino acids. The present study demonstrates a stereoselective reduction of the amide carbonyl moiety leading to L-proline derivatives in which all of the ring methylenes are stereoselectively labeled with deuterium.