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Chiral Auxiliary Controlled Asymmetric Synthesis of Tertiary Alcohols
M. I. Antczak, F. Cai, J. M. Ready*
The University of Texas Southwestern Medical Center at Dallas, USA
18 March 2011 (online)
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.