Hydrometallation-asymmetric conjugate addition: application to complex molecule synthesis

Abstract

Copper catalysis allows alkyl zirconium species, generated in situ from alkenes, to undergo conjugate addition reactions. A hydrometallation-catalytic asymmetric 1,4-addition was used to synthesize either enantiomer of a natural product in one step from commercially available materials. Hydrometallation-addition sequences applied to steroids containing a cross-conjugated dienone or 1,6-acceptor give highly functionalized products.