Synthesis of optically active amino sugar derivatives using catalytic enantioselective hetero-Diels–Alder reactions

A new synthetic method for the formation of optically active amino sugars using catalytic enantioselective inverse-electron demand hetero-Diels–Alder reactions of γ-amino-protected β,γ-unsaturated α-keto esters with vinyl ethers is presented; the catalytic reactions proceed in good yield with high diastereo- and enantioselectivity and fully control of the stereochemistry at the amino-carbon center.