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  • Title: Highly diastereoselective addition of nitromethane anion to chiral alpha-amidoalkylphenyl sulfones. Synthesis of optically active alpha-amino acid derivatives.
    Author: Foresti E, Palmieri G, Petrini M, Profeta R.
    Journal: Org Biomol Chem; 2003 Dec 07; 1(23):4275-81. PubMed ID: 14685331.
    Abstract:
    Optically active syn-alpha-amidoalkylphenyl sulfones can be prepared from chiral aldehydes in anhydrous conditions using benzenesulfinic acid. These sulfones in basic conditions give N-acylimines that react with sodium methanenitronate to afford the corresponding nitro adducts with high anti diastereoselectivity. PM3 semiempirical calculations provide a rationale for the observed opposite stereoselectivity. The obtained nitro derivatives undergo a Nef reaction followed by a methylation giving optically active beta-hydroxy-alpha-amino acid and alpha,beta-diamino acid esters in good yield. These amino acid derivatives are important building blocks for the preparation of biologically active compounds.
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