Bioinspired intramolecular spirocyclopropanation of quinones as an interrupted photoredox process
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F24%3A00598063" target="_blank" >RIV/61388963:_____/24:00598063 - isvavai.cz</a>
Result on the web
<a href="https://doi.org/10.1039/D4QO01291G" target="_blank" >https://doi.org/10.1039/D4QO01291G</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4qo01291g" target="_blank" >10.1039/d4qo01291g</a>
Alternative languages
Result language
angličtina
Original language name
Bioinspired intramolecular spirocyclopropanation of quinones as an interrupted photoredox process
Original language description
Intramolecular photoreactions of quinones can be interrupted by proton transfer using small molecules, such as trimethylamine N-oxide. This interruption de-excites the reactive spirocyclopropyl intermediates, the structures of which were for the first time confirmed by isolating them in their neutral form. The mild conditions of this process allow the conversion of a broad spectrum of quinones possessing linear and branched substituents to spirocyclopropanes in a catalytic, diastereoselective, and atom-conserving manner. Density functional theory (DFT) calculations were performed to investigate the possible reaction pathways and the origin of stereoselectivity. The established spirocyclopropanation route might be used to perform unconventional transformations of the side chains of quinones and to provide clues for the co-occurrence of certain natural quinones, hydroquinones, and spirocyclopropanes.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Organic Chemistry Frontiers
ISSN
2052-4129
e-ISSN
2052-4129
Volume of the periodical
11
Issue of the periodical within the volume
20
Country of publishing house
GB - UNITED KINGDOM
Number of pages
9
Pages from-to
5703-5711
UT code for WoS article
001298286600001
EID of the result in the Scopus database
2-s2.0-85202487305