Two directional electroorganic synthesis—electrochemical oxidation and application of a C2-symmetric building block

The C2-symmetric building block 1,2:5,6-di-N,O-carbonyl-1,6-diamino-3,4-O-isopropylidene-d-mannitol can be synthesized from d-mannitol in four steps using a nucleophilic substitution with cyanate and a subsequent cyclization in the final key step. The direct electrochemical oxidation of the resulting dioxazolidinone at 40 mA/cm2 in methanol at graphite electrodes with sodium benzene sulfonate as supporting electrolyte leads to the dimethoxylated product, which can be used in various diastereoselective amidoalkylation reactions. In all cases di-trans-stereoselectivity is observed.