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

摘要

Various substituted arylcuprates undergo stereocontrolled additions to a D-mannitol-derived gamma-alkoxy-alpha,beta-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.