Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkene dipeptide isosteres

Shinya Oishi; Ayumu Niida; Takae Kamano; Yoshihisa Miwa; Tooru Taga; Yoshihiko Odagaki; Nobuyuki Hamanaka; Mikio Yamamoto; Keiichi Ajito; Hirokazu Tamamura; Akira Otaka; Nobutaka Fujii

doi:10.1039/B203482D

Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkenedipeptide isosteres †

Shinya Oishi,^a Ayumu Niida,^a Takae Kamano,^a Yoshihisa Miwa,^a Tooru Taga,^a Yoshihiko Odagaki,^b Nobuyuki Hamanaka,^b Mikio Yamamoto,^c Keiichi Ajito,^c Hirokazu Tamamura,^a Akira Otaka^a and Nobutaka Fujii*^a

Author affiliations

* Corresponding authors

^a Graduate School of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto, Japan

^b Minase Research Institute, Ono Pharmaceutical Co. Ltd., Mishima-gun, Osaka, Japan

^c Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Kohoku-ku, Yokohama, Japan

Abstract

Organocopper-mediated alkylation of β-( N-Boc-2-oxo-1,3-oxazolidin-5-yl)-α,β-enoates has been intensively investigated. Alkylation proceeded regio- and stereoselectively by anti- S_N2′ ring-opening to provide a new route to the synthesis of ψ[( E)-CH [double bond, length as m-dash] CH]-, ψ[( E)-CMeCH]- and ψ[( E)-CMeCMe]- type alkene dipeptide isosteres from chiral amino acid derivatives. These resulting agents are potential mimetics of type II and type II′ β-turn substructure.

Journal of the Chemical Society, Perkin Transactions 1

Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkenedipeptide isosteres †

Abstract

Supplementary files

Article information

Download Citation

Permissions

Regio- and stereoselective ring-opening of chiral 1,3-oxazolidin-2-one derivatives by organocopper reagents provides novel access to di-, tri- and tetra-substituted alkene dipeptide isosteres

Search articles by author

Spotlight

Advertisements