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.
| Language | English |
|---|---|
| Pages | 1-6 |
| Number of pages | 6 |
| Journal | European Journal of Organic Chemistry |
| DOIs | |
| Publication status | E-pub ahead of print - 3 Jan 2019 |
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Keywords
- Allylation
- Boron reagents
- Heterocycles
- Indoles
- Synthetic methods
Cite this
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Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines. / Saya, Jordy M.; van Wordragen, Ellen D.H.; Orru, Romano V.A.; Ruijter, Eelco.
In: European Journal of Organic Chemistry, 03.01.2019, p. 1-6.Research output: Contribution to Journal › Article › Academic › peer-review
TY - JOUR
T1 - Mild and Practical Indole C2 Allylation by Allylboration of in situ Generated 3-Chloroindolenines
AU - Saya, Jordy M.
AU - van Wordragen, Ellen D.H.
AU - Orru, Romano V.A.
AU - Ruijter, Eelco
PY - 2019/1/3
Y1 - 2019/1/3
N2 - 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.
AB - 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.
KW - Allylation
KW - Boron reagents
KW - Heterocycles
KW - Indoles
KW - Synthetic methods
UR - http://www.scopus.com/inward/record.url?scp=85060245344&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85060245344&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201801745
DO - 10.1002/ejoc.201801745
M3 - Article
SP - 1
EP - 6
JO - European Journal of Organic Chemistry
T2 - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
ER -