Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles.
In: Chemical Communications, Jg. 55 (2019-12-21), Heft 98, S. 14757-14760
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Zugriff:
A Lewis acid-catalyzed insertion of unsymmetrical alkynes into electron-deficient alkenes was developed for the first time, and used to produce 34 hitherto unreported pentacyclic benzo[5,6]chromeno[2,3-b]indoles with generally good yields and complete stereoselectivity. A Yb(OTf) 3 -catalyzed reaction between o-alkynylnaphthols and 3-methyleneindolin-2-ones proceeded efficiently, and provided a simple and convergent protocol for alkyne difunctionalization via oxidant-free C–C double bond breaking/rearrangement. Mechanistic details of this domino process were derived by conducting systematic theoretical calculations. [ABSTRACT FROM AUTHOR]
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Titel: |
Completely regioselective insertion of unsymmetrical alkynes into electron-deficient alkenes for the synthesis of new pentacyclic indoles.
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Autor/in / Beteiligte Person: | Chen, Ke ; Xu, Ting ; Liang, Jian ; Zhou, Meng ; Zhang, Jie ; Hao, Wen-Juan ; Wang, Jianyi ; Tu, Shu-Jiang ; Jiang, Bo |
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Zeitschrift: | Chemical Communications, Jg. 55 (2019-12-21), Heft 98, S. 14757-14760 |
Veröffentlichung: | 2019 |
Medientyp: | academicJournal |
ISSN: | 1359-7345 (print) |
DOI: | 10.1039/c9cc08762a |
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