Dimeric Quinidine-Catalyzed Enantioselective Aminooxygenation of Oxindoles: An Organocatalytic Approach to 3-Hydroxyoxindole Derivatives

Tommy Bui, Nuno R. Candeias, Carlos F. Barbas

Research output: Contribution to journalArticleScientificpeer-review

159 Citations (Scopus)

Abstract

3-Hydroxyoxindoles are common structural motifs found in a vast array of natural and biologically active molecules. Most catalytic methods for the asymmetric syntheses of these compounds require the use of transition-metal catalysts. In contrast, alternative catalytic procedures involving organocatalysis are scarce. Herein we disclose a novel aminooxygenation of oxindoles with nitrosobenzene catalyzed by a newly designed quinidine dimer to afford the desired products in good yields with enantioselectivities up to 96%. These reactions allow one to construct a C-O bond at the C(3) position of oxindoles with the creation of an oxygen-containing tetrasubstituted chiral center and provide a new, general organocatalytic approach to the synthesis of 3-hydroxyoxindole derivatives.

Original languageEnglish
Pages (from-to)5574-5575
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number16
DOIs
Publication statusPublished - 28 Apr 2010
Externally publishedYes
Publication typeA1 Journal article-refereed

Keywords

  • ASYMMETRIC ADDITION
  • ARYLBORONIC ACIDS
  • ISATINS
  • HYDROXYLATION
  • NITROALKENES
  • 2-OXINDOLES
  • ALKALOIDS
  • ACCESS

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