Asymmetric Rh diene catalysis under confinement: isoxazole ring‐contraction in mesoporous solids
Abstract: Covalent immobilization of chiral dienes in mesoporous solids for asymmetric heterogeneous catalysis is highly attractive. In order to study confinement effects in bimolecular vs monomolecular reactions, a series of pseudo-C2-symmetrical tetrahydropentalenes was synthesized and immobilized via click reaction on different mesoporous solids (silica, carbon, covalent organic frameworks) and compared with homogeneous conditions. Two types of Rh-catalyzed reactions were studied: (a) bimolecular nucleophilic 1,2-additions of phenylboroxine to N-tosylimine and (b) monomolecular isomerization of isoxazole to 2H-azirne. Polar support materials performed better than non-polar ones. Under confinement, bimolecular reactions showed decreased yields, whereas yields in monomolecular reactions were only little affected. Regarding enantioselectivity the opposite trend was observed, i. e. effective enantiocontrol for bimolecular reactions but only little control for monomolecular reactions was found
- Location
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Deutsche Nationalbibliothek Frankfurt am Main
- Extent
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Online-Ressource
- Language
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Englisch
- Notes
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European journal of organic chemistry. - 27, 31 (2024) , e202400283, ISSN: 1099-0690
- Event
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Veröffentlichung
- (where)
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Freiburg
- (who)
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Universität
- (when)
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2024
- Creator
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Marshall, Max
Dilruba, Zarfishan
Beurer, Ann-Katrin
Bieck, Kira
Emmerling, Sebastian
Markus, Felix
Vogler, Charlotte
Ziegler, Felix
Fuhrer, Marina
Liu, Sherri S. Y.
Kousik, Shravan R.
Frey, Wolfgang
Traa, Yvonne
Bruckner, Johanna Ricarda
Plietker, Bernd
Buchmeiser, Michael R.
Ludwigs, Sabine
Naumann, Stefan
Atanasova, Petia
Lotsch, Bettina V.
Zens, Anna
Laschat, Sabine
- DOI
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10.1002/ejoc.202400283
- URN
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urn:nbn:de:bsz:25-freidok-2568354
- Rights
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Last update
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25.03.2025, 1:50 PM CET
Data provider
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.
Associated
- Marshall, Max
- Dilruba, Zarfishan
- Beurer, Ann-Katrin
- Bieck, Kira
- Emmerling, Sebastian
- Markus, Felix
- Vogler, Charlotte
- Ziegler, Felix
- Fuhrer, Marina
- Liu, Sherri S. Y.
- Kousik, Shravan R.
- Frey, Wolfgang
- Traa, Yvonne
- Bruckner, Johanna Ricarda
- Plietker, Bernd
- Buchmeiser, Michael R.
- Ludwigs, Sabine
- Naumann, Stefan
- Atanasova, Petia
- Lotsch, Bettina V.
- Zens, Anna
- Laschat, Sabine
- Universität
Time of origin
- 2024
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