RESUMEN

[reaction: see text] 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-SiMe(2)Ph bond.

Asunto(s)

1-Desoxinojirimicina/síntesis química , Piperidinas/síntesis química , 1-Desoxinojirimicina/química , Inhibidores Enzimáticos/síntesis química , Inhibidores Enzimáticos/química , Hidroxilación , Estructura Molecular , Oxidación-Reducción , Piperidinas/química , Estereoisomerismo