Asymmetric Michael reaction between a chiral α,β-dimethyl-β-enamino ester and α-substituted acrylates

An asymmetric Michael reaction between a chiral alpha,beta-dimethyl-beta-enamino ester derived from (S)-1-phenylethylamine and alpha-substituted acrylates is reported. Methyl acetamidoacrylate and methyl acetoxyacrylate furnished the expected Michael adduct with good ee's and de's. By contrast, an annulation process of the intermediary imine took place when using methyl methacrylates. (C) 2004 Elsevier Ltd. All rights reserved.