title: Diastereoselective synthesis of psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]- type dipeptide isosteres based on organocopper-mediated anti-S(N)2' reaction.
abstract: [reaction: see text] A straightforward synthetic route for the synthesis of diastereomerically pure psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]-type dipeptide isosteres was developed on the basis of regio- and stereoselective anti-S(N)2' alkylation of 3-(N-Boc-5-methyl-4-substituted-oxazolidin-2-on-5-yl)acrylates with organocopper reagents.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Oishi
authors.forename: Ayumu
authors.initials: A
authors.lastname: Niida
authors.forename: Takae
authors.initials: T
authors.lastname: Kamano
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Odagaki
authors.forename: Hirokazu
authors.initials: H
authors.lastname: Tamamura
authors.forename: Akira
authors.initials: A
authors.lastname: Otaka
authors.forename: Nobuyuki
authors.initials: N
authors.lastname: Hamanaka
authors.forename: Nobutaka
authors.initials: N
authors.lastname: Fujii
mesh_terms: D000478:Alkylation; D003300:Copper; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D004151:Dipeptides; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D003300:Copper