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Synlett 2024; 35(09): 983-988
DOI: 10.1055/s-0042-1751527
DOI: 10.1055/s-0042-1751527
cluster
Chemical Synthesis and Catalysis in Germany
Remote Enantioselective Epoxidation Reactions Catalyzed by Chiral Iron Porphyrin Complexes with a Hydrogen-Bonding Site
Financial support by the Deutsche Forschungsgemeinschaft (Ba 1372/23) is gratefully acknowledged.
Abstract
Iron porphyrin complexes, which were linked via a para-phenylethynyl group to a chiral scaffold with a lactam binding site, were probed as catalysts in the enantioselective epoxidation of 4-(ω-alkenyl)-quinolones. It was found that the 3-butenyl group in the substrate accounts for the highest enantioselectivity (up to 44% ee) and the absolute configuration of an oxirane product was elucidated by electron diffraction. A two-point hydrogen bond of the substrate to the catalyst is likely responsible for enantioface differentiation at a remote position. The study shows chirality transfer to be possible via four nonstereogenic carbon atoms between the binding site of the substrate and its reactive C=C double bond.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751527.
- Supporting Information
Publikationsverlauf
Eingereicht: 27. September 2023
Angenommen nach Revision: 30. Oktober 2023
Artikel online veröffentlicht:
30. November 2023
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Reviews:
For seminal contributions by Breslow and co-workers on remote functionalization, see:
Recent studies:
For early reports on the topic, see:
For reviews, see: