Back to Search Start Over

Titanium‐Catalyzed Intermolecular Hydroaminoalkylation of Allenes and Methylenecyclopropanes.

Authors :
Kaper, Tobias
Elma, Aylişa
Thye, Hermann
Knupe‐Wolfgang, Paula
Zimmering, René
Schmidtmann, Marc
Doye, Sven
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]

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