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Synfacts 2009(10): 1079-1079  
DOI: 10.1055/s-0029-1217903
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Synthesis of Spirooxindoles

Contributor(s): Victor Snieckus, Wei Gan
R. Shintani*, S.-y. Hayashi, M. Murakami, M. Takeda, T. Hayashi*
Kyoto University, Japan
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Publikationsdatum:
22. September 2009 (online)

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Significance

A stereoselective synthesis of spirooxindoles via decarboxylative cyclization of γ-methylidene-δ-valerolactones with N-methyl­isatins is described. Compared to ligand 1, the corresponding ligand 2 led to spirooxindoles with modest ee value and comparable yields and dr. The proposed mechanism indicates that the palladium-catalyzed decarboxylation of γ-methylidene-δ-valerolactones initiates the cyclization process and gives the target products.