Enantioselective transformations of 5-hydroxymethylfurfural via catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides

Abstract

A catalytic asymmetric 1,3-dipolar cycloaddition between iminoesters derived from 5-hydroxymethylfurfural (HMF) and different activated alkenes is reported. Excellent levels of diastereo and enantioselectivity were obtained when Fesulphos/Cu^I complex was used as catalyst. This metodology provides an effective and sustainable access to challenging enantioenriched heterocyclic scaffolds and represents one of the rare examples of catalytic asymmetric transformations using HMF as a starting material.