Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 132, Issue 16, Pages 5574-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja101032j
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Funding
- Skaggs Institute for Chemical Biology
- Fundacao para a Ciencia e Tecnologia [SFRH/BPD/46589/2008]
- Fundação para a Ciência e a Tecnologia [SFRH/BPD/46589/2008] Funding Source: FCT
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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.
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