Picolinamides and Iodoalkynes Enable Palladium-Catalyzed syn-Aminoalkynylation of Di- and Trisubstituted Alkenes to Give Pyrrolidines
dc.contributor.author
Müller, Nicolas
dc.contributor.author
Schreib, Benedikt S.
dc.contributor.author
Leutenegger, Sebastian U.
dc.contributor.author
Carreira, Erick M.
dc.date.accessioned
2022-09-19T08:31:30Z
dc.date.available
2022-05-27T04:12:56Z
dc.date.available
2022-05-27T12:35:10Z
dc.date.available
2022-09-19T08:31:30Z
dc.date.issued
2022
dc.identifier.issn
1433-7851
dc.identifier.issn
1521-3773
dc.identifier.issn
0570-0833
dc.identifier.other
10.1002/anie.202204535
en_US
dc.identifier.uri
http://hdl.handle.net/20.500.11850/549161
dc.identifier.doi
10.3929/ethz-b-000549161
dc.description.abstract
Palladium-catalyzed aminoalkynylation of electronically unbiased olefins with iodoalkynes is reported. The picolinamide auxiliary enables for the first time the syn-selective aminoalkynylation of mono-, di- and trisubstituted alkenes to afford the corresponding pyrrolidines in up to 97 % yield and as single diastereomers. Furthermore, through a C-H activation approach, the picolinamide allows the rapid synthesis of functionalized olefins, which are suitable cyclization precursors. Facile and orthogonal deprotection of the amides and (SiPr3)-Pr-i-acetylenes in the products, and a subsequent Pictet-Spengler reaction is demonstrated.
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
Alkenes
en_US
dc.subject
Alkynes
en_US
dc.subject
C-C Coupling
en_US
dc.subject
Nitrogen Heterocycles
en_US
dc.subject
Pd Catalysis
en_US
dc.title
Picolinamides and Iodoalkynes Enable Palladium-Catalyzed syn-Aminoalkynylation of Di- and Trisubstituted Alkenes to Give Pyrrolidines
en_US
dc.type
Journal Article
dc.rights.license
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International
dc.date.published
2022-04-21
ethz.journal.title
Angewandte Chemie. International Edition
ethz.journal.volume
61
en_US
ethz.journal.issue
38
en_US
ethz.journal.abbreviated
Angew. Chem. Int. Ed.
ethz.pages.start
e202204535
en_US
ethz.size
7 p.
en_US
ethz.version.deposit
publishedVersion
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::03511 - Carreira, Erick M. / Carreira, Erick M.
en_US
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::03511 - Carreira, Erick M. / Carreira, Erick M.
en_US
ethz.date.deposited
2022-05-27T04:14:01Z
ethz.source
WOS
ethz.eth
yes
en_US
ethz.availability
Open access
en_US
ethz.rosetta.installDate
2022-09-19T08:31:37Z
ethz.rosetta.lastUpdated
2023-02-07T06:23:26Z
ethz.rosetta.versionExported
true
ethz.COinS
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