Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine

Authors
van den Nieuwendijk, AMCH Kriek, NMAJ Brussee, J van Boom, JH van der Gen, A
Citation
Amch. Van Den Nieuwendijk et al., Stereoselective synthesis of (2R,5R)- and (2S,5R)-5-hydroxylysine, EUR J ORG C, (22), 2000, pp. 3683-3691
Citations number
41
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
1434193X → ACNP
Issue
22
Year of publication
2000
Pages
3683 - 3691
Database
ISI
SICI code
1434-193X(200011):22<3683:SSO(A(>2.0.ZU;2-7
Abstract
A stereoselective synthesis of (2S,5R)-5-hydroxylysine (1) and (2R,5R)-5-hy droxylysine (17), based on a concept involving Williams glycine template me thodology and (R)-hydroxynitrile lyase for the introduction of chirality at the alpha -position and the side-chain, respectively, is described. This s trategy offers an expeditious route towards orthogonally protected 5-hydrox ylysines.