Diastereoselective preparation of anti-β-amino alcohols via michael addition of alkoxide anions to nitroolefins and subsequent hydrogenation reaction

doi:10.1016/S0040-4039(01)80295-1

Tetrahedron Letters

Volume 30, Issue 6, 1989, Pages 731-734

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Abstract

Diastereoselective conjugate addition of benzylalkoxide anion to nitroolefins and subsequent hydrogenation reaction provide a new convenient method for the preparation of anti-β-amino alcohols.

Graphical abstract

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This chapter presents with conjugate additions of individual classes of nucleophiles relevant to nitroalkenes, alkenylsulfoxides, phosphonates and related compounds, quinones, alkenylsilanes, sulfides and selenides, and alkenylphosphonium salts. A variety of stabilized carbanions has been added to nitroalkenes. The additions are usually quite efficient and after Nef hydrolysis offer simple access to a wide range of 4-oxoalkanoates. The sodium salts of nitroalkanes may be added to nitroalkenes by simply mixing the two together in aqueous methanol. Cory's group has developed several methods for synthesizing tricyclic ketones from the addition of dienolates to nitroalkenes. Addition, followed by quenching with acetic acid gives good yields of the adduct, although with little stereoselectivity. The conjugate addition of carbanions, generated from zsocyanoacetates, to nitroalkenes leads to a pyrrolic product under very mild conditions. The suggested mechanism involves the following steps, shown for the synthesis of the trail marker pheromone of the Texas leaf-cutting ant, Atta texana. Conjugate additions to alkenylsulfoxides have become quite popular because of, firstly, their applications as chiral auxiliaries, especially when attached to cycloalkenones and secondly, because of the high stereoselectivity often obtained in these additions. They have also found use in annulation reactions. Additions to alkenyl, phosphonates have only been reported occasionally. Conjugate additions to quinones are unique in that, overall, they often replace a hydride. However, the mechanism is not one of the direct displacement of hydride, but, rather involves an aromatic intermediate, which is usually reoxidized, either during the reaction or in a separate step.
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Diastereoselective preparation of anti-β-amino alcohols via michael addition of alkoxide anions to nitroolefins and subsequent hydrogenation reaction

Abstract

Graphical abstract

J. Org. Chem.

Chem. Rev.

Chimia

Acc. Chem. Res.

Helv. Chim. Acta

Helv. Chim. Acta

J. Org. Chem.

Tetrahedron Lett.

Bull. Chem. Soc. Jpn.