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- Title
Titanium‐Catalyzed Intermolecular Hydroaminoalkylation of Allenes and Methylenecyclopropanes.
- Authors
Kaper, Tobias; Elma, Aylişa; Thye, Hermann; Knupe‐Wolfgang, Paula; Zimmering, René; Schmidtmann, Marc; Doye, Sven
- 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.
- Subjects
ALLENE; TITANIUM catalysts; SECONDARY amines; HYDROGEN atom; CYCLOPROPANE
- Publication
European Journal of Organic Chemistry, 2022, Vol 2022, Issue 45, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202200991