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.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

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

Contributors, Places and Time

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

Further information

• DOI: 10.1002/ange.202302416
• URN: urn:nbn:de:101:1-2023042515281408045670
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 10:51 AM CEST