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 u sing catalytic enantioselective inverse-electron demand hetero-Diels-Alder reactions of gamma-amino-protected beta,gamma-unsaturated alpha-keto esters with vinyl ethers is presented; the catalytic reactions proceed in good yi eld with high diastereo- and enantioselectivity and fully control of the st ereochemistry at the amino-carbon center.