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dc.contributor.author
Budinská, Alena
dc.contributor.author
Wennemers, Helma
dc.date.accessioned
2023-04-19T13:44:19Z
dc.date.available
2023-04-03T03:18:02Z
dc.date.available
2023-04-04T05:36:35Z
dc.date.available
2023-04-19T13:44:19Z
dc.date.issued
2023-04-17
dc.identifier.issn
1433-7851
dc.identifier.issn
1521-3773
dc.identifier.issn
0570-0833
dc.identifier.other
10.1002/anie.202300537
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/606165
dc.identifier.doi
10.3929/ethz-b-000606165
dc.description.abstract
Trifluoromethylsulfones (triflones) are useful compounds for synthesis and beyond. Yet, methods to access chiral triflones are scarce. Here, we present a mild and efficient organocatalytic method for the stereoselective synthesis of chiral triflones using alpha-aryl vinyl triflones, building blocks previously unexplored in asymmetric synthesis. The peptide-catalyzed reaction gives rise to a broad range of gamma-triflylaldehydes with two non-adjacent stereogenic centers in high yields and stereoselectivities. A catalyst-controlled stereoselective protonation following a C-C bond formation is key to control over the absolute and relative configuration. Straightforward derivatization of the products into, e.g., disubstituted delta-sultones, gamma-lactones, and pyrrolidine heterocycles highlights the synthetic versatility of the products.
en_US
dc.format
application/pdf
en_US
dc.language.iso
en
en_US
dc.publisher
Wiley-VCH
en_US
dc.rights.uri
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject
Non-Adjacent Stereocenters
en_US
dc.subject
Organocatalysis
en_US
dc.subject
Peptides
en_US
dc.subject
Stereoselective Synthesis
en_US
dc.subject
Triflones
en_US
dc.title
Organocatalytic Synthesis of Triflones Bearing Two Non-Adjacent Stereogenic Centers
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
dc.date.published
2023-02-27
ethz.journal.title
Angewandte Chemie. International Edition
ethz.journal.volume
62
en_US
ethz.journal.issue
17
en_US
ethz.journal.abbreviated
Angew. Chem. Int. Ed.
ethz.pages.start
e202300537
en_US
ethz.size
6 p.
en_US
ethz.version.deposit
publishedVersion
en_US
ethz.grant
Cell-Like"Molecular Assembly Lines": Programmable and Self-Regulating Reactors as Game-Changers in Chemical Synthesis
en_US
ethz.grant
Bioinspirierte Asymmetrische Katalyse (Fortsetzung 2020)
en_US
ethz.identifier.wos
ethz.identifier.scopus
ethz.publication.place
Weinheim
en_US
ethz.publication.status
published
en_US
ethz.leitzahl
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03940 - Wennemers, Helma / Wennemers, Helma
ethz.leitzahl.certified
ETH Zürich::00002 - ETH Zürich::00012 - Lehre und Forschung::00007 - Departemente::02020 - Dep. Chemie und Angewandte Biowiss. / Dep. of Chemistry and Applied Biosc.::02514 - Laboratorium für Organische Chemie / Laboratory of Organic Chemistry::03940 - Wennemers, Helma / Wennemers, Helma
ethz.grant.agreementno
862081
ethz.grant.agreementno
188729
ethz.grant.fundername
EC
ethz.grant.fundername
SNF
ethz.grant.funderDoi
10.13039/501100000780
ethz.grant.funderDoi
10.13039/501100001711
ethz.grant.program
H2020
ethz.grant.program
Projekte MINT
ethz.date.deposited
2023-04-03T03:18:18Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2023-04-19T13:44:21Z
ethz.rosetta.lastUpdated
2024-02-02T21:43:34Z
ethz.rosetta.versionExported
true
ethz.COinS
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