A general methodology for the asymmetric synthesis of 1-deoxyiminosugars

A general methodology for the stereoselective synthesis of 1-deoxymannojirimycin and its three other stereoisomers is described. The achiral olefin 6 was converted through the common olefin intermediate 12 to the target compounds in a highly stereocontrolled manner. The regioselective asymmetric aminohydroxylation (AA) and diastereoselective dihydroxylation reactions were used for the introduction of all four stereocenters in the targets, and the ring-closing metathesis (RCM) reaction was utilized for the construction of the required six-membered ring.