A Diastereoselective Catalytic Approach to Pentasubstituted Pyrrolidines by Tandem Anionic-Radical Cross-Over Reactions
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F22%3A00552859" target="_blank" >RIV/61388963:_____/22:00552859 - isvavai.cz</a>
Alternative codes found
RIV/00216208:11310/22:10454366
Result on the web
<a href="https://doi.org/10.1002/adsc.202101172" target="_blank" >https://doi.org/10.1002/adsc.202101172</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1002/adsc.202101172" target="_blank" >10.1002/adsc.202101172</a>
Alternative languages
Result language
angličtina
Original language name
A Diastereoselective Catalytic Approach to Pentasubstituted Pyrrolidines by Tandem Anionic-Radical Cross-Over Reactions
Original language description
Pentasubstituted pyrrolidines are ubiquitous constituents of natural products and drugs, however the access options to them especially with respect to absolute and relative stereochemistry are not well developed. We report an asymmetric synthesis of N,2,3,4,5-pentasubstituted pyrrolidines by oxidative single-electron transfer-catalyzed tandem aza-Michael addition/radical 5-exo cyclization/oxygenation reactions. The absolute stereochemistry is set by applying readily accessible chiral allylamines in asymmetric conjugate additions to various β-substituted-α,β-unsaturated esters, which dependent on the substituent R2 sets the configuration of the two stereocenters next to the amine function, whereas two more are diastereoselectively generated by the radical 5-exo cyclization step. This allows the diastereodivergent single-step synthesis of pyrrolidines with four contiguous stereogenic centers. The stereoselectivity is rationalized by a predictive model.
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
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
2022
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 & Catalysis
ISSN
1615-4150
e-ISSN
1615-4169
Volume of the periodical
364
Issue of the periodical within the volume
3
Country of publishing house
DE - GERMANY
Number of pages
8
Pages from-to
671-678
UT code for WoS article
000727403100001
EID of the result in the Scopus database
2-s2.0-85121393078