Stereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines |
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Authors: | Tobias Kaper Dennis Geik Felix Fornfeist Dr. Marc Schmidtmann Prof. Dr. Sven Doye |
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Affiliation: | Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9–11, 26129 Oldenburg, Germany |
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Abstract: | Intermolecular hydroaminoalkylation reactions of symmetrical and unsymmetrical alkynes with tertiary amines take place in the presence of catalytic amounts of TiBn4, Ph3C[B(C6F5)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. |
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Keywords: | alkynes amines C−H activation hydroaminoalkylation titanium |
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