Synfacts 2011(4): 0412-0412  
DOI: 10.1055/s-0030-1259646
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Auxiliary Controlled Asymmetric Synthesis of Tertiary Alcohols

Contributor(s): Mark Lautens, Stephen G. Newman
M. I. Antczak, F. Cai, J. M. Ready*
The University of Texas Southwestern Medical Center at Dallas, USA
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18. März 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.