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 γamino- and γ-carbamato-α,β-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.
Department of Chemistry, New Mexico Institute of Mining and Technology, Socorro, NM 87801, USA.
Shiva K
SK
Rastogi
Alexander
A
Kornienko