Intramolecular Michael addition of benzylamine to sugar derived α,β-unsaturated ester: a new diastereoselective synthesis of a higher homologue of 1-deoxy-L-ido-nojirimycin

Abstract

The diastereoselective intramolecular Michael addition of the benzylamine generated in situ from hemiacetal 3 leads to the lactone 4a with the required homoazasugar ring skeleton; reduction of the lactone functionality and removal of the protecting groups afford 1-deoxy-L-ido-homonojirimycin.