Stereoselective Synthesis of 1,n‐Dicarbonyl Compounds Through Palladium‐Catalyzed Ring Opening/Isomerization of Densely Substituted Cyclopropanols

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Abstract: We report a highly diastereoselective protocol for the synthesis of 1,4‐ and 1,5‐dicarbonyl compounds from densely substituted cyclopropanols. The methodology involves a palladium‐catalyzed ring opening reaction followed by a “metal‐walk” and oxidation of a remote hydroxyl group. The methodology represents a new application of cyclopropanols as initiation sites for chain walking remote functionalization. Importantly, this approach provides a straightforward access to highly valuable succinaldehyde derivatives bearing vicinal quaternary and tertiary stereocenters as single diastereomers.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Stereoselective Synthesis of 1,n‐Dicarbonyl Compounds Through Palladium‐Catalyzed Ring Opening/Isomerization of Densely Substituted Cyclopropanols ; day:27 ; month:11 ; year:2024 ; extent:6
Angewandte Chemie / International edition. International edition ; (27.11.2024) (gesamt 6)

Creator: Teschers, Charlotte S.
Cohen, Anthony
Marek, Ilan

DOI: 10.1002/anie.202421476

URN: urn:nbn:de:101:1-2411281336576.992997457886

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

Last update: 15.08.2025, 7:20 AM CEST

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Associated

Teschers, Charlotte S.
Cohen, Anthony
Marek, Ilan

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