Chiral Auxiliary Controlled Asymmetric Synthesis of Tertiary Alcohols

Significance

Addition of organometallic reagents to ketones and aldehydes is one of the most common methods for forming carbon-carbon bonds. The authors report the use of a chiral sulfoxide auxiliary to control the addition of organometallic reagents to aryl ketones. The resulting tertiary alcohols can be obtained with excellent enantiomeric excess after reductive lithiation of the sulf­oxide group and trapping with various electro-philes, such as proton, halide, carbon dioxide, and oxygen.