Organocatalytic Enantioselective Vinylcyclopropane‐Cyclopentene (VCP‐CP) Rearrangement

Abstract: We have demonstrated that the catalytic and enantioselective vinylcyclopropane‐cyclopentene rearrangement can be carried out on (vinylcyclopropyl) acetaldehydes through activation via enamine intermediates. The reaction makes use of racemic starting materials that, upon ring opening facilitated by the catalytic generation of a donor‐acceptor cyclopropane, deliver an acyclic iminium ion/dienolate intermediate in which all stereochemical information has been deleted. The final cyclization step forms the rearrangement product, showing that chirality transfer from the catalyst to the final compound is highly effective and leads to the stereocontrolled formation of a variety of structurally different cyclopentenes.

Angaben zum Objekt

• Standort: Deutsche Nationalbibliothek Frankfurt am Main
• Umfang: Online-Ressource
• Sprache: Englisch

Verweise und Beziehungen

• Erschienen in: Organocatalytic Enantioselective Vinylcyclopropane‐Cyclopentene (VCP‐CP) Rearrangement ; day:24 ; month:04 ; year:2023 ; extent:8 ; Angewandte Chemie ; (24.04.2023) (gesamt 8)

Beteiligte, Orts- und Zeitangaben

• Urheber: Garay, Gorka ; Hurtado, Josebe ; Pedrón, Manuel ; García, Lorena ; Reyes, Efraim ; Sánchez‐Díez, Eduardo ; Tejero, Tomás ; Carrillo, Luisa ; Merino, Pedro ; Vicario, Jose L.

Weitere Informationen

• DOI: 10.1002/ange.202302416
• URN: urn:nbn:de:101:1-2023042515281408045670
• Rechteinformation: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Letzte Aktualisierung: 14.08.2025, 10:51 MESZ