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Synfacts 2011(12): 1315-1315  
DOI: 10.1055/s-0031-1289328
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cu-Catalyzed Asymmetric α-Arylation of Carbonyls

Contributor(s): Hisashi Yamamoto, Jiajing Tan
J. S. Harvey, S. P. Simonovich, C. R. Jamison, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
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Publication History

Publication Date:
18 November 2011 (online)

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Significance

It remains a great challenge to directly install quaternary carbon stereocenters adjacent to a series of carbonyl moieties including ketones, lactones, esters, imides, and amides. The authors report an enantioselective α-arylation of both lactones and acyl oxazolidones by using a combination of diaryliodonium salts and the ­copper/BOX complex. The authors go on to display the value of this methodology in the asymmetric synthesis of the known medicinal agent (S)-naproxen.