Syntheses of iminolyxitols via tandem reduction-alkenylation of O'Donnell's Schiff bases

Article abstract of DOI:10.1016/S0040-4039(98)00495-X

The concise enantioselective synthesis of iminolyxitol glycosidase inhibitors starting from benzophenone imines of D-serine and L-alanine esters is very efficient. The reductive-alkenylation of the Schiff bases followed by substrate-directed dihydroxylation and amino dehydration gave the polyhydroxylated pyrrolidines in excellent overall yields (19.6% for 3 → 8. 9.9% for 2 → 13.).