657404-89-2Relevant academic research and scientific papers
Highly diastereoselective addition of nitromethane anion to chiral α-amidoalkylphenyl sulfones. Synthesis of optically active α-amino acid derivatives
Foresti, Elisabetta,Palmieri, Gianni,Petrini, Marino,Profeta, Roberto
, p. 4275 - 4281 (2007/10/03)
Optically active syn-α-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 methane-nitronate to afford the corresponding nitro adducts with high anti diastereoselectivity. PM3 semiempirical calculations provide a rationale for the observed opposite stereoselectivitity. The obtained nitro derivatives undergo a Nef reaction followed by a methylation giving optically active β-hydroxy-α-amino acid and α,β-diamino acid esters in good yield. These amino acid derivatives are important building blocks for the preparation of biologically active compounds.
