Bioinspired intramolecular spirocyclopropanation of quinones as an interrupted photoredox process

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F24%3A10490475" target="_blank" >RIV/00216208:11310/24:10490475 - isvavai.cz</a>
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=PoWvOeQ.W5" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=PoWvOeQ.W5</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1039/d4qo01291g" target="_blank" >10.1039/d4qo01291g</a>

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. Small molecules, such as trimethylamine N-oxide, interrupt intramolecular photoreactions of quinones by proton transfer and allow to convert a variety of quinones to spirocyclopropanes in a catalytic, diastereoselective, and atom-conserving manner.
Czech name
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Czech description
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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

Project
<a href="/en/project/GF21-39639L" target="_blank" >GF21-39639L: Catalytic Cyclotrimerization and C-C/C-H Functionalization Reactions in the Synthesis of Functional Molecules</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year
2024
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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