Cooperative benzylic-oxyallylic stabilized cations: regioselective construction of α-quaternary centers in ketone-derived compounds
Chemical Science, ISSN: 2041-6539, Vol: 6, Issue: 11, Page: 6312-6319
2015
- 25Citations
- 104Usage
- 17Captures
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Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
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Metrics Details
- Citations25
- Citation Indexes25
- 25
- CrossRef24
- Usage104
- Downloads96
- Abstract Views8
- Captures17
- Readers17
- 17
Article Description
We describe a novel reactivity of benzylic-stabilized oxyallyl cations towards regioselective construction of carbon quaternary centers. These synthetically useful intermediates were readily generated upon ionization of aryl substituted α-hydroxy methylenol ethers with catalytic, mild Brønsted acid. The emerging unsymmetrical oxyallyl cations were then directly captured by indoles and other nucleophiles with exquisite control of regioselectivity, predictably at the electrophilic carbon bearing the alkyl substituent to produce highly functionalized, value-added enol ethers.
Bibliographic Details
http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=84944076823&origin=inward; http://dx.doi.org/10.1039/c5sc01914a; http://www.ncbi.nlm.nih.gov/pubmed/30090249; https://xlink.rsc.org/?DOI=C5SC01914A; http://xlink.rsc.org/?DOI=C5SC01914A; http://pubs.rsc.org/en/content/articlepdf/2015/SC/C5SC01914A; https://repository.lsu.edu/chemistry_pubs/574; https://repository.lsu.edu/cgi/viewcontent.cgi?article=1574&context=chemistry_pubs; https://digitalcommons.lsu.edu/chemistry_pubs/574; https://digitalcommons.lsu.edu/cgi/viewcontent.cgi?article=1574&context=chemistry_pubs; https://dx.doi.org/10.1039/c5sc01914a; https://pubs.rsc.org/en/content/articlelanding/2015/sc/c5sc01914a; https://pubs.rsc.org/en/content/articlelanding/2015/SC/C5SC01914A; https://pubs.rsc.org/en/content/articlepdf/2015/sc/c5sc01914a; https://pubs.rsc.org/en/content/articlehtml/2015/sc/c5sc01914a; http://pubs.rsc.org/en/Content/ArticleLanding/2015/SC/C5SC01914A
Royal Society of Chemistry (RSC)
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