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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.

Type

Journal article

Journal

Journal of the Chemical Society, Perkin Transactions 1

Publication Date

01/12/1994

Volume

9

Pages

1141 - 1147