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.

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