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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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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)
- Urheber
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Kaper, Tobias
Elma, Aylişa
Thye, Hermann
Knupe‐Wolfgang, Paula
Zimmering, René
Schmidtmann, Marc
Doye, Sven
- DOI
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10.1002/ejoc.202200991
- URN
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urn:nbn:de:101:1-2022092015122765199263
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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15.08.2025, 07:22 MESZ
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Beteiligte
- Kaper, Tobias
- Elma, Aylişa
- Thye, Hermann
- Knupe‐Wolfgang, Paula
- Zimmering, René
- Schmidtmann, Marc
- Doye, Sven