A solution to the stereochemical problems posed by amaryllidaceae constituents using a highly syn-selective arylcuprate conjugate addition to γ-amino and γ-carbamato-α,β-enoates

Various substituted arylcuprates undergo stereocontrolled additions to L-serine-derived gamma-amino- and gamma-carbamato-alpha,beta-enoates with high syn-selectivities. The stereochemical outcome of these reactions is fully consistent with the reductive elimination-based model proposed previously. This method is well suited for the preparation of a broad range of biologically active amaryllidaceae constituents and their aromatic analogues. (c) 2006 Elsevier Ltd. All rights reserved.