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

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Richard P. Hsung, John F. Quinn, Brian A. Weisenberg, William D. Wulff, Glenn P. A. Yap and Arnold L. Rheingold


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.


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