title: Diastereoselective synthesis of (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives.
abstract: [reaction: see text] Herein, we report a diastereoselective synthesis of the natural product (2S,5R)-5-hydroxypipecolic acid and 6-substituted derivatives thereof. The key step in the synthetic sequence is a novel highly diastereoselective epoxidation reaction of an enantiomerically pure cyclic enamide intermediate.
authors.affiliation: Chiralix B.V., P.O. Box 31070, 6503 CB Nijmegen, The Netherlands.
authors.forename: Peter N M
authors.initials: PN
authors.lastname: Botman
authors.forename: F Jan
authors.initials: FJ
authors.lastname: Dommerholt
authors.forename: René
authors.initials: R
authors.lastname: de Gelder
authors.forename: Quirinus B
authors.initials: QB
authors.lastname: Broxterman
authors.forename: Hans E
authors.initials: HE
authors.lastname: Schoemaker
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
authors.forename: Richard H
authors.initials: RH
authors.lastname: Blaauw
mesh_terms: D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D010875:Pipecolic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010875:Pipecolic Acids; C053574:5-hydroxypipecolic acid