<div class="csl-bib-body">
<div class="csl-entry">Scharinger, F., Weil, M., Schnürch, M., & Schröder, K. (2024, May 27). <i>Advancing Synthetic Pathways for Nitrogen Heterocyclic Drug Candidates: One-Step Asymmetric Diazabicycloalkane Synthesis</i> [Poster Presentation]. TCH Science Days, Austria. http://hdl.handle.net/20.500.12708/208094</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/208094
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dc.description.abstract
Diazabicycloalkanes and pyridazines are highly valued nitrogen-containing heterocycles, esteemed for their extensive range of biological activities. Symmetric diazabicycloalkanes, characterized by a unique structure comprising a condensed bicyclic ring system bridged by two nitrogen atoms, are particularly intriguing. Despite established methods for synthesizing chiral pyridazines, the one-step synthesis of condensed diazabicycloalkanes remains a considerable challenge. Current methodologies predominantly employ multi-step synthesis which not only suffers from low atom economy but also imposes limitations on the final heterocyclic structure.
Our novel approach accomplishes the one-step synthesis of chiral diazabicycloalkanes by introducing the annulated ring system within a single reaction step. This is achievable through the use of an organocatalytic aza-Michael/aldol process involving the enal substrate class. By employing simple diphenylethylendiamine frameworks as dual activation organocatalysts, we effectively engage both substrate and reagent, resulting in moderate to high yields and high enantioselectivities (ranging from 80-98%). Remarkably, our method demonstrates excellent functional group tolerance across various enals and allows for in situ modification of the product aldehyde motif without compromising enantioselectivity. Furthermore, through adjustment of the quantity of acid cocatalyst, we showcase the tunability of enantioselectivity and yield, offering multiple optimization pathways for this synthetic methodology.1
(1) Scharinger, F.; Weil, M.; Schnürch, M.; Bica‐Schröder, K. Synthesis of Chiral Diazabicycloalkanes via Organocatalytic Aza‐Michael/Aldol Reaction. Adv. Synth. Catal. 2024, 366 (1), 49–55. https://doi.org/10.1002/adsc.202301125.
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dc.description.sponsorship
European Commission
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dc.language.iso
en
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dc.subject
asymmetric synthesis
en
dc.subject
organocatalysis
en
dc.subject
nitrogen heterocycles
en
dc.title
Advancing Synthetic Pathways for Nitrogen Heterocyclic Drug Candidates: One-Step Asymmetric Diazabicycloalkane Synthesis
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.relation.grantno
7465546 - 04/12/2019
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dc.type.category
Poster Presentation
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tuw.project.title
Kontinourliche Umsetzung von CO2 in ionischen Flüssigkeiten
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tuw.researchinfrastructure
Röntgenzentrum
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tuw.researchTopic.id
M6
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tuw.researchTopic.name
Biological and Bioactive Materials
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tuw.researchTopic.value
100
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tuw.publication.orgunit
E163 - Institut für Angewandte Synthesechemie
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tuw.author.orcid
0000-0001-8690-3785
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tuw.author.orcid
0000-0001-5235-9910
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tuw.author.orcid
0000-0003-2946-9294
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tuw.author.orcid
0000-0002-2515-9873
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tuw.event.name
TCH Science Days
de
tuw.event.startdate
27-05-2024
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tuw.event.enddate
29-05-2024
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tuw.event.online
On Site
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tuw.event.type
Event for scientific audience
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tuw.event.country
AT
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tuw.event.presenter
Scharinger, Fabian
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tuw.event.track
Single Track
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wb.sciencebranch
Chemie
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wb.sciencebranch
Chemische Verfahrenstechnik
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wb.sciencebranch
Pharmazie, Pharmakologie, Toxikologie
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wb.sciencebranch.oefos
1040
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wb.sciencebranch.oefos
2040
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wb.sciencebranch.oefos
3012
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wb.sciencebranch.value
60
-
wb.sciencebranch.value
20
-
wb.sciencebranch.value
20
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item.fulltext
no Fulltext
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item.openairecristype
http://purl.org/coar/resource_type/c_18co
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item.openairetype
conference poster not in proceedings
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item.grantfulltext
none
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item.cerifentitytype
Publications
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item.languageiso639-1
en
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crisitem.project.funder
European Commission
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crisitem.project.grantno
7465546 - 04/12/2019
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crisitem.author.dept
E163-03-5 - Forschungsgruppe Nachhaltige organische Synthese und Katalyse
