A New Insight into the Stereoelectronic Control of the Pd-0-Catalyzed Allylic Substitution: Application for the Synthesis of Multisubstituted Pyran-2-ones via an Unusual 1,3-Transposition
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F19%3A00507868" target="_blank" >RIV/61388963:_____/19:00507868 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11160/19:10396875 RIV/00216208:11310/19:10396875
Result on the web
<a href="https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201900323" target="_blank" >https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.201900323</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201900323" target="_blank" >10.1002/chem.201900323</a>
Alternative languages
Result language
angličtina
Original language name
A New Insight into the Stereoelectronic Control of the Pd-0-Catalyzed Allylic Substitution: Application for the Synthesis of Multisubstituted Pyran-2-ones via an Unusual 1,3-Transposition
Original language description
Pyran-2-ones 3 undergo a novel Pd-0-catalyzed 1,3-rearrangement to afford isomers 6. The reaction proceeds via an eta(2)-Pd complex, the pyramidalization of which (confirmed by quantum chemistry calculations) offers a favorable antiperiplanar alignment of the Pd-C and allylic C-O bonds (C), thus allowing the formation of an eta(3)-Pd intermediate. Subsequent rotation and rate-limiting recombination with the carboxylate arm then gives isomeric pyran-2-ones 6. The calculated free energies reproduce the observed kinetics semi-quantitatively.
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
10403 - Physical chemistry
Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2019
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Chemistry - A European Journal
ISSN
0947-6539
e-ISSN
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Volume of the periodical
25
Issue of the periodical within the volume
34
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
8053-8060
UT code for WoS article
000474807200014
EID of the result in the Scopus database
2-s2.0-85065641205