title: Synthesis and asymmetric hydrogenation of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione.
abstract: The synthesis of (3E)-1-benzyl-3-[(2-oxopyridin-1(2H)-yl)methylidene]piperidine-2,6-dione 5 from N-benzylglutarimide was achieved in three steps. The asymmetric hydrogenation of 4 gave either the product of partial reduction (10) or full reduction (13), depending on the catalyst which was employed, in high ee in each case. Attempts at asymmetric transfer hydrogenation (ATH) of resulted in formation of a racemic product.
authors.affiliation: Department of Chemistry, The University of Warwick, Coventry, CV4 7AL, UK.
authors.forename: Alexander A
authors.initials: AA
authors.lastname: Bisset
authors.forename: Akira
authors.initials: A
authors.lastname: Shiibashi
authors.forename: Jasmine L
authors.initials: JL
authors.lastname: Desmond
authors.forename: Allan
authors.initials: A
authors.lastname: Dishington
authors.forename: Teyrnon
authors.initials: T
authors.lastname: Jones
authors.forename: Guy J
authors.initials: GJ
authors.lastname: Clarkson
authors.forename: Takao
authors.initials: T
authors.lastname: Ikariya
authors.forename: Martin
authors.initials: M
authors.lastname: Wills
mesh_terms: D001593:Benzyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006865:Hydrogenation; D015394:Molecular Structure; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C580609:(3E)-1-benzyl-3-((2-oxopyridin-1(2H)-yl)methylidene)piperidine-2,6-dione; D001593:Benzyl Compounds; D010881:Piperidones; C007864:glutarimide