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Synfacts 2009(3): 0300-0300
DOI: 10.1055/s-0028-1087783
DOI: 10.1055/s-0028-1087783
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium-Catalyzed Coupling of Allylic Acetates and Arylboronic Acids
H. Ohmiya, Y. Makida, T. Tanaka, M. Sawamura*
Hokkaido University, Sapporo, Japan
Further Information
Publication History
Publication Date:
19 February 2009 (online)
Significance
The authors discovered a new palladium-catalyzed coupling reaction of various allylic acetates and arylboronic acids. This reaction generates allyl-aryl compounds in high γ- and E-selectivity. Optically pure allylic acetates provide products with excellent syn-selectivity via α-to-γ chirality transfer. A possible mechanism for the transformation is proposed.