Application of the Brook Rearrangement in Tandem with Single Electron Transfer Oxidative and Radical Processes

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00523805" target="_blank" >RIV/61388963:_____/20:00523805 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/20:10420980
Result on the web
<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202000126" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.202000126</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.202000126" target="_blank" >10.1002/ejoc.202000126</a>

Result language
angličtina
Original language name
Application of the Brook Rearrangement in Tandem with Single Electron Transfer Oxidative and Radical Processes
Original language description
Merging rearrangement with radical reactions is a largely unexplored field but may hold promise for approaching scaffolds that are inaccessible by other methodology. Here a tandem nucleophilic substitution/Brook rearrangement/single-electron transfer oxidation/radical oxygenation strategy is presented, through which alpha,gamma-dioxygenated epsilon,zeta-unsaturated amides are efficiently prepared in a single step from enantiomerically enriched allylepoxides and 2-silylacetamides. The resulting compounds can be easily transformed by persistent radical effect-based 5-exo-trig or 6-endo-trig radical cyclization reactions to functionalized carbocycles bearing three or four stereocenters. The stereochemical outcome of the cyclization reactions can predicted by the Beckwith-Houk model. The cyclic compounds can be easily diversified by post-cyclization modifications. The tandem process can be further extended by an acylation step leading to beta-dicarbonyl enolates, which were also transformed to cyclopentane and cyclohexane derivatives under oxidative conditions.
Czech name
—
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
—
OECD FORD branch
10401 - Organic chemistry

Project
<a href="/en/project/GA16-18513S" target="_blank" >GA16-18513S: Tandem Sigmatropic Rearrangement/Radical Reactions - A New Productive Alliance in Organic Chemistry</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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