N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate 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%2F61388963%3A_____%2F16%3A00463910" target="_blank" >RIV/61388963:_____/16:00463910 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/16:10327773
Result on the web
<a href="http://dx.doi.org/10.1002/ejoc.201600621" target="_blank" >http://dx.doi.org/10.1002/ejoc.201600621</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/ejoc.201600621" target="_blank" >10.1002/ejoc.201600621</a>
Alternative languages
Result language
angličtina
Original language name
N,2,3,4-Tetrasubstituted Pyrrolidines through Tandem Lithium Amide Conjugate Addition/Radical Cyclization/Oxygenation Reactions
Original language description
Enantioselective syntheses of densely functionalized pyrrolidines deriving their chirality from (R)-1-(phenyl) ethylamine are reported. Allylic amines and beta-substituted-alpha, beta-unsaturated esters are used as the building blocks in this one-pot reaction. Single electron transfer (SET) oxidation served to merge the reactivities of anionic enolate and radical intermediates. Ferrocenium hexafluorophosphate, which is easy to prepare, store and handle, was applied as SET oxidant and persistent free radical TEMPO served as the oxygenating agent introducing a protected hydroxy function, which proved to be beneficial for further derivatization. Exclusive 2,3-trans and up to 6: 1 3,4-cis/trans diastereoselectivities were achieved in the targeted tetrasubstituted pyrrolidines.
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
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
European Journal of Organic Chemistry
ISSN
1434-193X
e-ISSN
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Volume of the periodical
2016
Issue of the periodical within the volume
22
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
3862-3871
UT code for WoS article
000382768400027
EID of the result in the Scopus database
2-s2.0-84978394400