Synfacts 2009(3): 0300-0300  
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

Contributor(s): Hisashi Yamamoto, Zhi Li
H. Ohmiya, Y. Makida, T. Tanaka, M. Sawamura*
Hokkaido University, Sapporo, Japan
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Publikationsverlauf

Publikationsdatum:
19. Februar 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.