STEREOSELECTIVE SYNTHESIS OF (2S,3S,4R,5S)-PROLINE-3,4,5-D(3)

Authors
OBA M TERAUCHI T HASHIMOTO J TANAKA T NISHIYAMA K
Citation
M. Oba et al., STEREOSELECTIVE SYNTHESIS OF (2S,3S,4R,5S)-PROLINE-3,4,5-D(3), Tetrahedron letters, 38(31), 1997, pp. 5515-5518
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
31
Year of publication
1997
Pages
5515 - 5518
Database
ISI
SICI code
0040-4039(1997)38:31<5515:SSO(>2.0.ZU;2-9
Abstract
A catalytic deuteration of protected 3,4-dehydro-L-proline using RuCl2 (PPh3)(3) followed by RuO4-oxidatian gave a 3,4-dideuterated L-pyroglu tamic acid derivative which is considered to be a promising precursor far various deuterated amino acids. The present study demonstrates a s tereoselective reduction of the amide carbonyl moiety leading to L-pro line derivatives in which all of the ring methylenes are stereoselecti vely labeled with deuterium. (C) 1997 Elsevier Science Ltd.