A Practical Synthesis of C2-Symmetric Chiral Binaphthyl Ketone Catalyst

All articles of this category A practical synthesis of 11-membered C 2 -symmetric binaphthyl ketone ( R )- 1 , a catalyst for asymmetric epoxidation, was developed. (±)-1,1'-Binaphthyl-2,2'-dicarboxylic acid [(±)- 6 ] was efficiently resolved by ( R )-(-)-1-cyclohexylethylamine 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 °C provided the desired chiral ketone ( R )- 1 in 61-63% yield without need for high dilution techniques. catalysts - asymmetric epoxidation - dioxiranes - macrocycles - optical resolution