A Stereoselective Route toward Polyhydoxylated Piperidines. A Total Synthesis of (±)-Deoxymannojirimycin

A chemo- and stereoselective palladium-catalyzed amination of silylated butenediol dicarbonates has allowed for the introduction of a glycine
moiety to obtain a desired functionalized epoxysilane. A stereoselective aldolization then delivered the piperidine ring which may be used as
a precursor for the synthesis of a variety of polyhydroxylated azasugars. This efficient approach has been illustrated by the synthesis of
1-deoxymannojirimycin including a stereoselective reduction with LAH and a Tamao−Fleming oxidation of a C−SiMe2Ph bond.