Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
Abstract: A novel class of highly activated donor‐acceptor cyclopropanes bearing only a single, vinylogous acceptor is presented. These strained moieties readily undergo cycloadditions with aldehydes, ketones, thioketones, nitriles, naphth‐2‐ols and various other substrates to yield the corresponding carbo‐ and heterocycles. Diastereocontrol can be achieved through the choice of catalyst (Brønsted or Lewis acid). The formation of tetrahydrofurans was shown to be highly enantiospecific when chiral cyclopropanes are employed. A series of mechanistic and kinetic experiments was conducted to elucidate a plausible catalytic cycle and to rationalize the stereochemical outcome.
- Location
-
Deutsche Nationalbibliothek Frankfurt am Main
- Extent
-
Online-Ressource
- Language
-
Englisch
- Bibliographic citation
-
Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor ; day:30 ; month:11 ; year:2022 ; extent:1
Angewandte Chemie ; (30.11.2022) (gesamt 1)
- Creator
- DOI
-
10.1002/ange.202214390
- URN
-
urn:nbn:de:101:1-2022120114072380406753
- Rights
-
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
-
08.09.1974, 12:00 AM CET
Data provider
This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Ahlburg, Nils L.
- Hergert, Oliver
- Jones, Peter G.
- Werz, Daniel B.
Other Objects (12)
Donor‐acceptor cyclopropanes: activation enabled by a single, vinylogous acceptor
Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Donor‐Acceptor Activation of Carbon Dioxide
Organic Donor‐Acceptor Systems for Photocatalysis
Donor-acceptor cyclopropanes in organic synthesis
A mechanochromic donor-acceptor torsional spring
Donor-acceptor polymers for organic solar cells
Dioxygen compatible electron donor-acceptor catalytic system and its enabled aerobic oxygenation
(Spectro-)electrochemical characterisation of bridged donor-acceptor compounds
Robust Red‐Absorbing Donor‐Acceptor Stenhouse Adduct Photoswitches
Donor‐acceptor cyclopropanes: activation enabled by a single, vinylogous acceptor
Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Donor‐Acceptor Activation of Carbon Dioxide
Organic Donor‐Acceptor Systems for Photocatalysis
Donor-acceptor cyclopropanes in organic synthesis
A mechanochromic donor-acceptor torsional spring
Donor-acceptor polymers for organic solar cells
Dioxygen compatible electron donor-acceptor catalytic system and its enabled aerobic oxygenation
(Spectro-)electrochemical characterisation of bridged donor-acceptor compounds
Robust Red‐Absorbing Donor‐Acceptor Stenhouse Adduct Photoswitches
Donor‐acceptor cyclopropanes: activation enabled by a single, vinylogous acceptor
Donor‐Acceptor Cyclopropanes: Activation Enabled by a Single, Vinylogous Acceptor
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Halogenated Donor–Acceptor Cyclopropanes as Donor–Acceptor Cyclopropene Surrogates
Donor‐Acceptor Activation of Carbon Dioxide
Organic Donor‐Acceptor Systems for Photocatalysis
Donor-acceptor cyclopropanes in organic synthesis
A mechanochromic donor-acceptor torsional spring
Donor-acceptor polymers for organic solar cells
Dioxygen compatible electron donor-acceptor catalytic system and its enabled aerobic oxygenation
(Spectro-)electrochemical characterisation of bridged donor-acceptor compounds