Diastereoselective Synthesis of Cyclopropanes from Carbon Pronucleophiles and Alkenes

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Abstract: Cyclopropanes are desirable structural motifs with valuable applications in drug discovery and beyond. Established alkene cyclopropanation methods give rise to cyclopropanes with a limited array of substituents, are difficult to scale, or both. Herein, we disclose a new cyclopropane synthesis through the formal coupling of abundant carbon pronucleophiles and unactivated alkenes. This strategy exploits dicationic adducts derived from electrolysis of thianthrene in the presence of alkene substrates. We find that these dielectrophiles undergo cyclopropanation with methylene pronucleophiles via alkenyl thianthrenium intermediates. This protocol is scalable, proceeds with high diastereoselectivity, and tolerates diverse functional groups on both the alkene and pronucleophile coupling partners. To validate the utility of this new procedure, we prepared an array of substituted analogs of an established cyclopropane that is en route to multiple pharmaceuticals.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Diastereoselective Synthesis of Cyclopropanes from Carbon Pronucleophiles and Alkenes ; day:17 ; month:04 ; year:2023 ; extent:8
Angewandte Chemie / International edition. International edition ; (17.04.2023) (gesamt 8)

Creator: Kim, Min Ji
Wang, Diana J.
Targos, Karina
Garcia, Uriel A.
Harris, Alison F.
Guzei, Ilia A.
Wickens, Zachary K.

DOI: 10.1002/anie.202303032

URN: urn:nbn:de:101:1-2023041815010772904156

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:45 AM CEST

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Associated

Kim, Min Ji
Wang, Diana J.
Targos, Karina
Garcia, Uriel A.
Harris, Alison F.
Guzei, Ilia A.
Wickens, Zachary K.

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