1,4-Asymmetric induction in the formation of cyclohexadienones by chirality transfer from a transiently installed chromium–stereospecific electrocyclic ring closure of a metal complexed vinyl ketene

Abstract

The cyclohexadienone annulation of a β,β-disubstituted vinyl chromium carbene complex and a chiral prop-2-ynylic ether results in high 1,4-asymmetric induction at the newly formed quaternary carbon; the stereochemical information from the prop-2-ynylic ether is initially transfered to the chromium coordination sphere and then to the quaternary carbon of the cyclohexa-2,4-dienone.