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Synfacts 2009(7): 0766-0766  
DOI: 10.1055/s-0029-1217285
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed α-Arylation-Vinylation of Arylmandelic Acid Derivatives

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
L. Jiang, S. Weist, S. Jansat*
Institute of Chemical Research of Catalonia, Tarragona, Spain
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

The dioxolane derivative of mandelic acid (1) has been used as a substrate as well as an auxiliary in various Pd-catalyzed reactions. The authors report the first α-arylation and vinylation of this chiral substrate to provide products containing a chiral all-carbon stereocenter. Use of standard hydrolysis or reductive procedures provide chiral α-hydroxy acids and 1,2-diols, respectively, in high optical purities.