Titanium‐Catalyzed Intermolecular Hydroaminoalkylation of Allenes and Methylenecyclopropanes

Abstract: Intermolecular hydroaminoalkylation reactions of 1,1‐ and 1,3‐disubstituted allenes as well as methylenecyclopropanes with secondary amines can be achieved in the presence of a 2,6‐bis (phenylamino) pyridinato titanium catalyst at 140 °C within 2–8 h. Corresponding reactions of allenes with N‐benzylanilines deliver branched allylamine products in very good yields (up to 83 %) and with branched‐linear‐ratios between 75: 25 and 95: 5. In contrast, bicyclic methylenecyclopropanes undergo hydroaminoalkylation with N‐benzylanilines or N‐alkylbenzylamines to give linear products in good to excellent yields (up to 98 %) with perfect regio‐ and diastereoselectivity. The corresponding 1,2,3‐trisubstituted (2‐aminoethyl) cyclopropane products exhibit a structurally interesting cis‐orientation of all three cyclopropane hydrogen atoms.

Object Details

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

References and Relationships

• Bibliographic citation: Titanium‐Catalyzed Intermolecular Hydroaminoalkylation of Allenes and Methylenecyclopropanes ; day:19 ; month:09 ; year:2022 ; extent:1 ; European journal of organic chemistry ; (19.09.2022) (gesamt 1)

Contributors, Places and Time

• Creator: Kaper, Tobias ; Elma, Aylişa ; Thye, Hermann ; Knupe‐Wolfgang, Paula ; Zimmering, René ; Schmidtmann, Marc ; Doye, Sven

Further information

• DOI: 10.1002/ejoc.202200991
• URN: urn:nbn:de:101:1-2022092015122765199263
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 15.08.2025, 7:22 AM CEST