Abstract
C2 allylation of indole derivatives is a challenging but important transformation given the biological relevance of the products. Herein we report a selective C2 allylation strategy that proceeds via allylboration of in situ-generated 3-chloroindolenines. The reaction is mild, practical, and compatible with a wide range of C3-substituted indoles. As allylboronates are readily accessible from commercial precursors, various substituted allyl moieties can be introduced using the same protocol. To showcase the utility of this method we applied it to the synthesis of the natural product, tryprostatin B.
| Original language | English |
|---|---|
| Pages (from-to) | 5156-5160 |
| Number of pages | 5 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2019 |
| Issue number | 31-32 |
| Early online date | 3 Jan 2019 |
| DOIs | |
| Publication status | Published - 1 Sep 2019 |
Keywords
- Allylation
- Boron reagents
- Heterocycles
- Indoles
- Synthetic methods
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Saya, J. M., van Wordragen, E. D. H., Orru, R. V. A., & Ruijter, E. (2019). Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines. European Journal of Organic Chemistry, 2019(31-32), 5156-5160. https://doi.org/10.1002/ejoc.201801745