A Chiral Relay Race: Stereoselective Synthesis of Axially Chiral Biaryl Diketones through Ring-Opening of Optical Dihydrophenan-threne-9,10-diols.

We report herein a point-to-axial chirality transfer reaction of optical dihydrophenanthrene-9,10-diols for the synthesis of axially chiral diketones. Two sets of conditions, namely a basic t BuOK/air atmosphere and an acidic NaClO/ n -Bu 4 NHSO 4 , were developed to oxidatively cleave the C-C bond, resulting in the formation of axially chiral biaryl diketones. Finally, brief synthetic applications of the obtained chiral aryl diketones were demonstrated.