<div class="csl-bib-body">
<div class="csl-entry">Pálvölgyi, Á. M., Smith, J., Schnürch, M., & Schröder, K. (2022, July 3). <i>ASYMMETRIC TRANSFER HYDROGENATIONS AND ALPHA ALLYLATIONS USING FLEXIBLE OR RACEMIC PHOSPHORIC ACIDS VIA COUNTERION-ENHANCED CATALYSIS</i> [Poster Presentation]. 17th Belgian Organic Synthesis Symposium, Namur, Belgium. http://hdl.handle.net/20.500.12708/152422</div>
</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/152422
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dc.description
As a conceptional spin-off of the aforementioned ACDC, we envisioned of using readily available chiral amines
in combination with flexible or racemic phosphoric acids for asymmetric catalytic purposes. With both catalyst
counterparts being natural-derived, such a “counterion enhanced catalytic” strategy would have the advantage of
cheap and simple catalyst synthesis and therefore could provide a valuable alternative to current state-of-the-art
methodologies. Using a thymol-derived racemic phosphoric acid in combination with chiral amines, we have
developed efficient organocatalysts for the asymmetric transfer hydrogenation of enones and for the direct
asymmetric α-allylation of aldehydes, respectively. For both reactions, excellent yields and enantioselectivities
were obtained. These results showed that such a concept can be successfully adapted both to iminium– and
enamine-catalytic reactions. Moreover, we also showed that sterically demanding, but simple flexible or racemic
phosphoric acids might provide a good alternative to the field of ACDC.
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dc.description.abstract
Forging new C-C stereocenters is one of the major challenges in modern organic chemistry. In this field, classical iminium and enamine catalysis became indispensable tools, enabling tremendous advancements for the asymmetric functionalization of both saturated and unsaturated carbonyl species. [1,2]As an add-on to classical aminocatalysis, B. List et al. pioneered the field of Asymmetric Counteranion Directed Catalysis (ACDC),providing remarkable examples for the β-functionalization of enals and enones by relying on catalyst salts of chiral/achiral amines and enantiomerically pure phosphoric acids.[3] While these elegant protocols provided indeed excellent yields and enantioselectivities, the catalyst synthesis often suffered from multi-step synthesis
and tedious separations, resulting in rather expensive catalytic systems.
As a conceptional spin-off of the aforementioned ACDC, we envisioned of using readily available chiral amines in combination with flexible or racemic phosphoric acids for asymmetric catalytic purposes. With both catalyst counterparts being natural-derived, such a “counterion enhanced catalytic” strategy would have the advantage of cheap and simple catalyst synthesis and therefore could provide a valuable alternative to current state-of-the-art methodologies. Using a thymol-derived racemic phosphoric acid in combination with chiral amines, we have developed efficient organocatalysts for the asymmetric transfer hydrogenation of enones and for the direct asymmetric α-allylation of aldehydes, respectively. For both reactions, excellent yields and enantioselectivities were obtained. These results showed that such a concept can be successfully adapted both to iminium– and enamine-catalytic reactions. Moreover, we also showed that sterically demanding, but simple flexible or racemic
phosphoric acids might provide a good alternative to the field of ACDC.
en
dc.language.iso
en
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dc.subject
catalysis
en
dc.subject
organocatalysis
en
dc.subject
transfer hydrogenation
en
dc.title
ASYMMETRIC TRANSFER HYDROGENATIONS AND ALPHA ALLYLATIONS USING FLEXIBLE OR RACEMIC PHOSPHORIC ACIDS VIA COUNTERION-ENHANCED CATALYSIS
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.contributor.affiliation
Technische Universität Wien Fakultät für Technische Chemie
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dc.rights.holder
Ádám Márk Pálvölgyi
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dc.type.category
Poster Presentation
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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
-
tuw.author.orcid
0000-0001-8138-0831
-
tuw.author.orcid
0000-0003-2946-9294
-
tuw.author.orcid
0000-0002-2515-9873
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tuw.event.name
17th Belgian Organic Synthesis Symposium
en
dc.description.sponsorshipexternal
European Unions Horizon 2020
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dc.relation.grantnoexternal
D163035-1002
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tuw.event.startdate
03-07-2022
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tuw.event.enddate
08-07-2022
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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.place
Namur
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tuw.event.country
BE
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tuw.event.institution
https://www.boss-symposium.org/
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tuw.event.presenter
Pálvölgyi, Ádám Márk
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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
-
wb.sciencebranch.oefos
2040
-
wb.sciencebranch.oefos
3012
-
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.cerifentitytype
Publications
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item.openairecristype
http://purl.org/coar/resource_type/c_18co
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item.languageiso639-1
en
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item.openairetype
conference poster not in proceedings
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item.grantfulltext
none
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crisitem.author.dept
E163-03-5 - Forschungsgruppe Nachhaltige organische Synthese und Katalyse
-
crisitem.author.dept
E302-01 - Forschungsbereich Thermodynamik und Wärmetechnik
-
crisitem.author.dept
E163 - Institut für Angewandte Synthesechemie
-
crisitem.author.dept
E163-03-5 - Forschungsgruppe Nachhaltige organische Synthese und Katalyse
-
crisitem.author.orcid
0000-0003-2946-9294
-
crisitem.author.orcid
0000-0002-2515-9873
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
-
crisitem.author.parentorg
E302 - Institut für Energietechnik und Thermodynamik
-
crisitem.author.parentorg
E150 - Fakultät für Technische Chemie
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie