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Synfacts 2010(7): 0785-0785
DOI: 10.1055/s-0029-1220075
DOI: 10.1055/s-0029-1220075
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag
Stuttgart ˙ New York
Rhodium-Catalyzed Asymmetric Synthesis of Spirocarbocycles
R. Shintani*, S. Isobe, M. Takeda, T. Hayashi*
Kyoto University, Japan
Further Information
Publication History
Publication Date:
22 June 2010 (online)
Significance
Enantiomerically pure spirocycles with a quaternary spirocarbon stereocenter are found in natural products, biologically active compounds, and chiral ligands for asymmetric catalysis. The authors report an asymmetric rhodium-catalyzed addition of sodium tetraarylborates 2 to alkyne-tethered 2-cycloalken-1-ones 1 for the construction of the spirocyclic product 3 via an arylrhodation-1,4-rhodium migration sequence. Good yield and excellent ee values can be obtained using the chiral diene ligand (R,R)-Bn-bod*.