13048-78-7Relevant academic research and scientific papers
Asymmetric Synthesis of syn-α-Alkyl-β-amino Acids
Davies, Stephen G.,Ichihara, Osamu,Walters, Iain A. S.
, p. 1141 - 1148 (2007/10/02)
An investigation into the reactivity of the highly stereoselective conjugate nucleophile lithium N-benzyl-N-α-methylbenzylamide 1 with α-alkyl-α,β-unsaturated esters has led to the development of a versatile asymmetric synthesis of syn-α-alkyl-β-amino acids.By performing the conjugate additions in toluene and diluting the reaction mixtures with THF prior to quenching of the reactions with the hindered acid, 2,6-di-tert-butylphenol 13, the product syn-α-alkyl-β-amino esters may be generated in good yield and with excellent stereocontrol.Several examples illustrate the ease with which these products may be debenzylated and hydrolysed to afford homochiral syn-α-alkyl-β-amino acids.
