title: Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis.
abstract: An efficient route for the synthesis of all four diastereomers of PMP-protected α-amino-γ-butyrolacton to access γ-hydroxynorvaline was established. The asymmetric key steps comprise an organocatalytic Mannich reaction and an enzymatic ketone reduction. Three reaction steps could be integrated in a one-pot process, using 2-PrOH both as solvent and as reducing agent. The sequential construction of stereogenic centres gave access to each of the four stereoisomers in high yield and with excellent stereocontrol.
authors.affiliation: Department of Chemistry, University of Graz, NAWI Graz, Heinrichstraße 28, A-8010-Graz, Austria. wolfgang.kroutil@uni-graz.at robert.simon@uni-graz.at.
authors.forename: Robert C
authors.initials: RC
authors.lastname: Simon
authors.forename: Eduardo
authors.initials: E
authors.lastname: Busto
authors.forename: Joerg H
authors.initials: JH
authors.lastname: Schrittwieser
authors.forename: Johann H
authors.initials: JH
authors.lastname: Sattler
authors.forename: Jörg
authors.initials: J
authors.lastname: Pietruszka
authors.forename: Kurt
authors.initials: K
authors.lastname: Faber
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Kroutil
mesh_terms: D019840:2-Propanol / Q000737:chemistry; D000429:Alcohol Oxidoreductases / Q000737:chemistry / Q000378:metabolism; D001665:Binding Sites; D055162:Biocatalysis; D002090:Butyrophenones / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D062105:Molecular Docking Simulation; D009249:NADP / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D017434:Protein Structure, Tertiary; D019163:Reducing Agents / Q000737:chemistry; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014633:Valine / Q000031:analogs & derivatives* / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D002090:Butyrophenones; D007659:Ketones; D019163:Reducing Agents; D012997:Solvents; D009249:NADP; C005313:norvaline; D000429:Alcohol Oxidoreductases; D014633:Valine; D019840:2-Propanol