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
Further Information

Publication History

Publication Date:
19 August 2011 (online)


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.