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

✍ Scribed by Makoto Oba; Tsutomu Terauchi; Jun Hashimoto; Tomohiro Tanaka; Kozaburo Nishiyama

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 227 KB
Volume: 38
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(97)01189-1

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✦ Synopsis

A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCI2(PPh3) 3 followed by RuO~-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.

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