Flexible and Stereocontrolled Synthesis of Azasugars with Novel Substitution Patterns

Abstract

Polyhydroxylated piperidines (azasugars) with novel substitution patterns are synthesized in high diastereo- and enantiomeric excesses by α,α′ -double alkylation of 2,2-dimethyl- 1,3-dioxan-5-one using the SAMP-/RAMP-hydrazone method and subsequent piperidine ring formation through reductive amination.