Highly Functionalized Cyclopentane Derivatives by Tandem Michael Addition/Radical Cyclization/Oxygenation Reactions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216208%3A11310%2F15%3A10313138" target="_blank" >RIV/00216208:11310/15:10313138 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/15:00446086
Result on the web
<a href="http://dx.doi.org/10.1002/chem.201500424" target="_blank" >http://dx.doi.org/10.1002/chem.201500424</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/chem.201500424" target="_blank" >10.1002/chem.201500424</a>
Alternative languages
Result language
angličtina
Original language name
Highly Functionalized Cyclopentane Derivatives by Tandem Michael Addition/Radical Cyclization/Oxygenation Reactions
Original language description
Densely functionalized cyclopentane derivatives with up to four consecutive stereocenters are assembled by a tandem Michael addition/single-electron transfer oxidation/radical cyclization/oxygenation strategy mediated by ferrocenium hexafluorophosphate,a recyclable, less toxic single-electron transfer oxidant. Ester enolates were coupled with alpha-benzylidene and alpha-alkylidene beta-dicarbonyl compounds with switchable diastereoselectivity. This pivotal steering element subsequently controls the diastereoselectivity of the radical cyclization step. The substitution pattern of the radical cyclization acceptor enables a switch of the cyclization mode from a 5-exo pattern for terminally substituted olefin units to a 6-endo mode for internally substituted acceptors. The oxidative anionic/radical strategy also allows efficient termination by oxygenation with the free radical 2,2,6,6-tetramethyl-1-piperidinoxyl, and two C-C bonds and one C-O bond are thus formed in the sequence. A stereo
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CC - Organic chemistry
OECD FORD branch
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Result continuities
Project
<a href="/en/project/GA13-40188S" target="_blank" >GA13-40188S: Conceptually new catalytic traceless asymmetric oxidative anionic-radical domino reactions</a><br>
Continuities
Z - Vyzkumny zamer (s odkazem do CEZ)<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2015
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
21
Issue of the periodical within the volume
27
Country of publishing house
DE - GERMANY
Number of pages
12
Pages from-to
9877-9888
UT code for WoS article
000357027300038
EID of the result in the Scopus database
2-s2.0-84930153276