Diastereoselective synthesis of psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]- type dipeptide isosteres based on organocopper-mediated anti-S(N)2' reaction

Shinya Oishi; Ayumu Niida; Takae Kamano; Yoshihiko Odagaki; Hirokazu Tamamura; Akira Otaka; Nobuyuki Hamanaka; Nobutaka Fujii

doi:10.1021/ol016835b

Diastereoselective synthesis of psi[(E)-CMe=CH]- and psi[(E)-CMe=CMe]- type dipeptide isosteres based on organocopper-mediated anti-S(N)2' reaction

Org Lett. 2002 Apr 4;4(7):1055-8. doi: 10.1021/ol016835b.

Authors

Shinya Oishi¹, Ayumu Niida, Takae Kamano, Yoshihiko Odagaki, Hirokazu Tamamura, Akira Otaka, Nobuyuki Hamanaka, Nobutaka Fujii

Affiliation

¹ Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, 606-8501, Japan.

PMID: 11922781
DOI: 10.1021/ol016835b

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkylation
Copper*
Dipeptides / chemical synthesis
Dipeptides / chemistry*
Indicators and Reagents
Organometallic Compounds / chemistry*
Stereoisomerism

Substances

Dipeptides
Indicators and Reagents
Organometallic Compounds
Copper