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Titanium‐Catalyzed Intermolecular Hydroaminoalkylation of Allenes and Methylenecyclopropanes.
- Source :
- European Journal of Organic Chemistry; 12/6/2022, Vol. 2022 Issue 45, p1-7, 7p
- Publication Year :
- 2022
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- ALLENE
TITANIUM catalysts
SECONDARY amines
HYDROGEN atom
CYCLOPROPANE
Subjects
Details
- Language :
- English
- ISSN :
- 1434193X
- Volume :
- 2022
- Issue :
- 45
- Database :
- Complementary Index
- Journal :
- European Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 160676624
- Full Text :
- https://doi.org/10.1002/ejoc.202200991