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Synfacts 2011(11): 1219-1219  
DOI: 10.1055/s-0031-1289189
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Pd-Catalyzed Asymmetric Intramolecular Arylation of α-Keto Amides

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
L. Yin, M. Kanai*, M. Shibasaki*
The University of Tokyo and Institute of Microbial Chemistry, Tokyo, Japan
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

This work describes the Pd-catalyzed enantioselective intramolecular arylation of α-keto anilides which provided access to 3-hydroxy-2-oxindoles with 53-93% yield and 82-99% ee. Poorly accessible derivatives of aliphatic α-keto anilides could also be prepared. Furthermore, the methodology could be expanded to the synthesis of 4-hydroxydihydroquinolinones, which serve as useful building blocks for drug candidates; no easy catalytic asymmetric route to these compounds existed before this work. A putative reaction mechanism was proposed.