Facile synthesis of N-Boc-(2S,5R)-5-(1 '-hydroxy-1 '-methylethyl)proline

Authors
Wang, Q Dau, METH Sasaki, NA Potier, P
Citation
Q. Wang et al., Facile synthesis of N-Boc-(2S,5R)-5-(1 '-hydroxy-1 '-methylethyl)proline, TETRAHEDRON, 57(30), 2001, pp. 6455-6462
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
30
Year of publication
2001
Pages
6455 - 6462
Database
ISI
SICI code
0040-4020(20010723)57:30<6455:FSON''>2.0.ZU;2-4
Abstract
Coupling of chiral 1-O-benzylglycerol-2,3-bistriflate with trilithiated chi ral 2-N-Boc-3-phenylsulfonylpropan-1-ol derivative constitutes an efficient route to chiral C-5 substituted prolines which can potentially induce cis Xaa-Pro peptide bond conformation. A straightforward seven-step synthesis o f the title compound is described. (C) 2001 Elsevier Science Ltd. All right s reserved.