Desymmetrisation of Dienylsilanes. Stereoselective Access to Cyclitols and Carba-Sugars

Abstract

The diastereo- and enantioselective functionalisation of 1,4-cyclohexadienylsilanes using Sharpless asymmetric dihydroxylation and aminohydroxylation offers a straightforward access to various classes of potent inhibitors of glycosidases. The scope and limitation of this desymmetrisation method is illustrated here with the synthesis of various conduritols, carba-sugars and carba-C-disaccharides.