title: Highly enantioselective synthesis of rigid, quaternary 1,4-benzodiazepine-2,5-diones derived from proline.
abstract: [reaction: see text] Proline-derived 1,4-benzodiazepine-2,5-diones are extremely useful scaffolds in medicinal chemistry. In this paper, we describe a protocol for retentive C3 alkylation of these materials, thus accomplishing the direct synthesis of enantiopure quaternary 1,4-benzodiazepine-2,5-diones. The high enantioselectivities (up to 99.5%) are attributed to memory of chirality.
authors.affiliation: Department of Chemistry, Virginia Tech, Blacksburg, Virginia 24061, USA.
authors.forename: Stephanie
authors.initials: S
authors.lastname: MacQuarrie-Hunter
authors.forename: Paul R
authors.initials: PR
authors.lastname: Carlier
mesh_terms: D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001570:Benzodiazepinones; D011392:Proline