Divergent approach to imino sugar C-glycosides using imino glycals: application to the stereocontrolled synthesis of (+)-deoxoprosophylline

Abstract

Tri-O-acetyl imino glucal 2 is readily made and shown to undergo a variety of Lewis acid mediated carbon-carbon bond forming reactions at C-1 of the piperidine nucleus. In all the reactions studied, the beta-anomer is predominant.