Core-Structure-Motivated Design of a Phosphine-Catalyzed [3 + 2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles
2011; American Chemical Society; Volume: 133; Issue: 13 Linguagem: Inglês
10.1021/ja110147w
ISSN1943-2984
AutoresBin Tan, Nuno R. Candeias, Carlos F. Barbas,
Tópico(s)Synthetic Organic Chemistry Methods
ResumoA novel organocatalytic asymmetric [3 + 2] cycloaddition reaction between methyleneindolinones and allylic compounds yielding complex spirocyclopentaneoxindoles has been developed. It provides extraordinary levels of enantioselective control involving a chiral phosphine as a nucleophilic organocatalyst. Simple precursors were used under mild conditions to construct oxindole derivatives with high enantiopurity and structural diversity. This method should be useful in medicinal chemistry and diversity-oriented syntheses of these intriguing compounds.
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