Diastereoselective synthesis of psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]- type dipeptide isosteres based on organocopper-mediated anti-S(N)2' reaction.
[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.
Oishi
Shinya
S
Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan.
Niida
Ayumu
A
Kamano
Takae
T
Odagaki
Yoshihiko
Y
Tamamura
Hirokazu
H
Otaka
Akira
A
Hamanaka
Nobuyuki
N
Fujii
Nobutaka
N
D000478:Alkylation; D003300:Copper; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D007202:Indicators and Reagents; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D004151:Dipeptides; D007202:Indicators and Reagents; D009942:Organometallic Compounds; D003300:Copper