Highly diastereoselective synthesis of densely functionalized cyclopentanoids by intramolecular azomethine imine cycloadditions in sugar templates

Abstract

Conversion of a sugar to a δ,ε-unsaturated aldehyde, and subsequent condensation of the aldehyde moiety with BnNHNHCO₂Et, yields the respective azomethine imine intermediate dipole which adds intramolecularly to the existing double bond, thus generating a bicyclic adduct with high diastereoselectivity.