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 language | English |
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Pages (from-to) | 5574-5575 |
Number of pages | 2 |
Journal | Journal of the American Chemical Society |
Volume | 132 |
Issue number | 16 |
DOIs | |
Publication status | Published - 28 Apr 2010 |
Externally published | Yes |
Publication type | A1 Journal article-refereed |
Keywords
- ASYMMETRIC ADDITION
- ARYLBORONIC ACIDS
- ISATINS
- HYDROXYLATION
- NITROALKENES
- 2-OXINDOLES
- ALKALOIDS
- ACCESS