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Synfacts 2009(8): 0888-0888  
DOI: 10.1055/s-0029-1217433
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Hydroxy-2-oxindoles via Cu(I)F-Catalyzed Protocols

Contributor(s): Mark Lautens, Jacki Kitching
D. Tomita, K. Yamatsugu, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

Further to previous research concerning the enantioselective Cu(I)F-catalyzed arylation and alkenylation of aldehydes and activated ketones using silanes and boronates as nucleophiles (J. Am. Chem. Soc. 2005, 127, 4138; Tetrahedron Lett. 2006, 47, 8083; Chem. Asian J. 2006, 1, 161), the authors now describe an efficient protocol for the arylation and alkenylation of statin substrates. Furthermore, the first catalytic asymmetric synthesis of the biologically active compound, SM-130686, was achieved (17 steps, 10% overall yield) using an intramolecular variant of this protocol.