Stereoselective N-Heterocyclic-Carbene-Catalyzed Spiroannulation as an Access Towards Spirobenzofuranone-Fused Cyclohexenones
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11160%2F24%3A10490254" target="_blank" >RIV/00216208:11160/24:10490254 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/24:10490254
Result on the web
<a href="https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=ZpgoGakndl" target="_blank" >https://verso.is.cuni.cz/pub/verso.fpl?fname=obd_publikace_handle&handle=ZpgoGakndl</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.202401111" target="_blank" >10.1002/adsc.202401111</a>
Alternative languages
Result language
angličtina
Original language name
Stereoselective N-Heterocyclic-Carbene-Catalyzed Spiroannulation as an Access Towards Spirobenzofuranone-Fused Cyclohexenones
Original language description
In this work, we present an organocatalytic spiroannulation method that provides access to spirocyclic benzofuran-2-ones. The reaction proceeds via the generation of an azolium dienolate from an alpha-bromo-alpha,beta-unsaturated aldehyde using a chiral N-heterocyclic carbene, followed by annulation with benzofuran-2-one-derived alkenes. The resulting chiral spirobenzofuranone-fused cyclohexenones were obtained in 77-99% ee and dr from 1.2:1 to 20:1. The utility of the protocol was underscored by gram-scale reaction and follow-up transformations.
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
<a href="/en/project/GA22-11234S" target="_blank" >GA22-11234S: New Horizons of Catalysis with N-Heterocyclic Carbenes (NHC2)</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
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
Advanced Synthesis and Catalysis
ISSN
1615-4150
e-ISSN
1615-4169
Volume of the periodical
366
Issue of the periodical within the volume
24
Country of publishing house
FR - FRANCE
Number of pages
7
Pages from-to
5008-5014
UT code for WoS article
001345155700001
EID of the result in the Scopus database
2-s2.0-85207780209