Highly anti-selective conjugate addition of arylcuprates to a γ-alkoxy-α,β-enoate. A new method to address stereochemical challenges presented by Amaryllidaceae alkaloids

Various substituted arylcuprates undergo stereocontrolled additions to a d-mannitol-derived γ-alkoxy-α,β-enoate with exclusive anti-selectivity. The method is well suited for the preparation of a broad range of biologically active Amaryllidaceae alkaloids and their aromatic analogues. A model accounting for the stereochemical outcome of this process is presented.