title: Enantioselective deprotonative ring contraction of N1-methyl-N4-Boc-benzo[e][1,4]diazepine-2,5-diones.
abstract: N1-Methyl-N4-Boc-benzo[e][1,4]diazepine-2,5-diones were prepared in good yield and high stereochemical purity from five amino acids. Upon deprotonation, these compounds undergo ring contraction to the corresponding quinolone-2,4-diones with high enantioselectivity, providing efficient entry to a potentially useful drug scaffold. Mechanistic commentary and comparisons to related reactions are provided.
authors.affiliation: Department of Chemistry, Virginia Tech , Blacksburg, Virginia 24061, United States.
authors.forename: Stephanie A
authors.initials: SA
authors.lastname: Antolak
authors.forename: Zhong-Ke
authors.initials: ZK
authors.lastname: Yao
authors.forename: Gary M
authors.initials: GM
authors.lastname: Richoux
authors.forename: Carla
authors.initials: C
authors.lastname: Slebodnick
authors.forename: Paul R
authors.initials: PR
authors.lastname: Carlier
mesh_terms: D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001381:Azepines; D007659:Ketones; D015363:Quinolones