title: Diastereoselective synthesis of psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres by organocopper-mediated anti-S(N)2' reaction.
abstract: [reaction: see text] Acyclic psi[(E)-CH=CMe]- and psi[(Z)-CH=CMe]-type dipeptide isosteres were efficiently synthesized. In a key reaction, alpha-alkylation of gamma-mesyloxy-beta-methyl-alpha,beta-unsaturated esters with organocyanocuprates in diethyl ether or tetrahydrofuran preferentially afforded the psi[(E)-CH=CMe]- or psi[(Z)-CH=CMe]-isomer, respectively, via anti-S(N)2' mechanism.
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: Takae
authors.initials: T
authors.lastname: Kamano
authors.forename: Ayumu
authors.initials: A
authors.lastname: Niida
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