A practical synthesis of C-2-symmetric chiral binaphthyl ketone catalyst

A practical synthesis of 11-membered C-2-symmetric binaphthyl ketone (R)-1, a catalyst for asymmetric epoxidation, was developed. (+/-)-1,1'-Binaphthy l-2,2'-dicarboxylic acid [(+/-)-6] was efficiently resolved by (R)-(-)-1-cy clohexylethylamine to give (R)-6 in >99% ee and in 38% yield. Condensation of the acid chloride derived from (R)-6 with 1,3-dihydroxyacetone dimer at 60-70 degreesC provided the desired chiral ketone (R)-1 in 61-63% yield wit hout need for high dilution techniques.