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Synfacts 2010(1): 0065-0065  
DOI: 10.1055/s-0029-1218509
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Stereoablative Alkylation of 3-Halooxindoles

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
S. Ma, X. Han, S. Krishan, S. C. Virgil, B. M. Stoltz*
California Institute of Technology, Pasadena, and Beckman Research Institute at City of Hope, Duarte, USA
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Publication History

Publication Date:
21 December 2009 (online)

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Significance

The 3,3-disubstituted oxindole moiety is prevalent in a variety of biologically active molecules. In most enantioselective methods for the construction of this motif, the oxindole unit functions as nucleophile. In the present report, oxindole serves as an electrophile for the coupling with malonate nucleophiles. Racemic 3-bromo- or 3-chlorooxindoles containing alkyl/alkyl ether or aromatic substituents at the 3-position are alkylated in a stereoablative process in high ee.