Core-Structure-Motivated Design of a Phosphine-Catalyzed [3+2] Cycloaddition Reaction: Enantioselective Syntheses of Spirocyclopenteneoxindoles

Bin Tan, Nuno R. Candeias, Carlos F. Barbas

    Research output: Contribution to journalArticleScientificpeer-review

    411 Citations (Scopus)

    Abstract

    A 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.

    Original languageEnglish
    Pages (from-to)4672-4675
    Number of pages4
    JournalJournal of the American Chemical Society
    Volume133
    Issue number13
    DOIs
    Publication statusPublished - 6 Apr 2011
    Publication typeA1 Journal article-refereed

    Funding

    Research support from the Skaggs Institute for Chemical Biology is gratefully acknowledged. N.R.C. thanks Fundacao para a Ciencia e Tecnologia (SFRH/BPD/46589/2008) for financial support. We also thank Dr. A. L. Rheingold for the X-ray crystallographic analysis.

    Keywords

    • ASYMMETRIC ASSEMBLY REACTIONS
    • MODIFIED ALLYLIC COMPOUNDS
    • PHOSPHORUS YLIDE REACTION
    • MICHAEL-HENRY REACTIONS
    • BAYLIS-HILLMAN REACTION
    • DIELS-ALDER REACTIONS
    • ANNULATION REACTION
    • DOMINO REACTIONS
    • 4 STEREOCENTERS
    • MULTISUBSTITUTED CYCLOPENTANES

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