Stereoselective Synthesis of Tertiary Allylic Amines by Titanium‐Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
Tobias Kaper, Dennis Geik, Felix Fornfeist, Marc Schmidtmann, Sven Doye
Abstract
Abstract Intermolecular hydroaminoalkylation reactions of symmetrical and unsymmetrical alkynes with tertiary amines take place in the presence of catalytic amounts of TiBn 4 , Ph 3 C[B(C 6 F 5 ) 4 ], and a sterically demanding aminopyridinato ligand precursor. The resulting products, synthetically and pharmaceutically useful tertiary β,γ‐disubstituted allylic amines, are formed in convincing yields and with excellent stereoselectivity. Particularly promising for future applications is the fact that even the industrial side product trimethylamine can be used as a substrate.
Topics & Concepts
Allylic rearrangementStereoselectivityTrimethylamineSteric effectsChemistryCatalysisTertiary amineLigand (biochemistry)Substrate (aquarium)TitaniumIntermolecular forceCombinatorial chemistryOrganic chemistryMedicinal chemistryStereochemistryMoleculeOceanographyReceptorBiochemistryGeologyCarbon dioxide utilization in catalysisCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistry