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Synfacts 2011(9): 0991-0991  
DOI: 10.1055/s-0030-1260866
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Cyclization of 4-Alkenoic Acids via Oxidative Allylic C-H Esterification

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
K. Takenaka, M. Akita, Y. Tanigaki, S. Takizawa, H. Sasai*
Osaka University, Japan
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Publikationsdatum:
19. August 2011 (online)

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Significance

In this paper, the Pd-catalyzed enantioselective oxidative cyclization of 4-alkenoic acids is reported. The methodology is based on the SPRIX ligand, which has already shown unique reactivity in Pd-mediated asymmetric oxidative reactions. A range of products was obtained with moderate to excellent yields and enantioselectivities up to 82% ee. The use of other nucleophiles emphasized the crucial role of the carboxy group for efficient outcome.