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

摘要

Organocopper-mediated alkylation of β-(N-Boc-2-oxo-1,3-oxazolidin-5-yl)-α,β-enoates has been intensivelyninvestigated. Alkylation proceeded regio- and stereoselectively by anti-SN2u0001 ring-opening to provide a new route tonthe synthesis of ψ[(E)-CHu0002u0002CH]-, ψ[(E)-CMeu0002u0002CH]- and ψ[(E)-CMeu0002u0002CMe]- type alkene dipeptide isosteres fromnchiral amino acid derivatives. These resulting agents are potential mimetics of type II and type IIu0001 β-turnnsubstructure.