Diastereo- and Enantioselective Synthesis of Vicinal Amino Alcohols by Oxa Michael Addition ofN-Formylnorephedrine to Nitro Alkenes

The first intermolecular asymmetric oxa Michael additions with removable chirality information within the hydroxide source are reported. As enantiopure oxygen nucleophile functioning as chiral hydroxide equivalent N-formylnorephedrine (7) was used and conjugate additions to aliphatic (E)-nitro alkenes 2a–j were carried out in good yields (35-87%) and excellent diastereomeric excesses (de = 94–≥98%). After reduction of the nitro group and...