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

…, A Haertwig, G Raabe, J Runsink

Index: Enders, Dieter; Haertwig, Andreas; Raabe, Gerhard; Runsink, Jan European Journal of Organic Chemistry, 1998 , # 9 p. 1771 - 1792

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Citation Number: 5

Abstract

Abstract 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 ...