<div class="csl-bib-body">
<div class="csl-entry">Kaiser, M., Steinacher, M., Lukas, F., & Gärtner, P. (2024, July 3). <i>Carpe Diene! Europium-catalyzed [3,3] and [5,5] rearrangements of aryl-pentadienyl ethers</i> [Poster Presentation]. 18th Belgian Organic Synthesis Symposium, Liege, Belgium. https://doi.org/10.34726/8484</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/210349
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dc.identifier.uri
https://doi.org/10.34726/8484
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dc.description.abstract
In our recent study, we’ve developed a protocol for the europium-catalyzed rearrangement of aryl-dienyl ethers. In contrast to the well-investigated aryl-allyl ethers, these substrates were greatly overlooked by the scientific community despite their potential advantages. We found that the aryl substituent's position para to the phenol dictates the mode of rearrangement and product formation. When the para-position is substituted, the substrate undergoes a [3,3] rearrangement, resulting in an ortho-positioned prochiral branched diene. Conversely, an unoccupied para-position initiates a [5,5] rearrangement, yielding a linear conjugated diene product. The applied protocol proved a high functional group tolerance, and the obtained products were formed in good to excellent yields. The mechanism was elucidated by a series of deuterium-labeling and crossover experiments.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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dc.language.iso
en
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dc.rights.uri
http://rightsstatements.org/vocab/InC/1.0/
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dc.subject
5,5 rearrangement
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dc.subject
catalysis
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dc.title
Carpe Diene! Europium-catalyzed [3,3] and [5,5] rearrangements of aryl-pentadienyl ethers
