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Stereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines.

ABSTRACT: Intermolecular hydroaminoalkylation reactions of symmetrical and unsymmetrical alkynes with tertiary amines take place in the presence of catalytic amounts of TiBn₄ , Ph₃ C[B(C₆ F₅ )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.

SUBMITTER: Kaper T

PROVIDER: S-EPMC9303398 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Stereoselective Synthesis of Tertiary Allylic Amines by Titanium-Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines.

Kaper Tobias T Geik Dennis D Fornfeist Felix F Schmidtmann Marc M Doye Sven S

Chemistry (Weinheim an der Bergstrasse, Germany) 20220125 10

Intermolecular hydroaminoalkylation reactions of symmetrical and unsymmetrical alkynes with tertiary amines take place in the presence of catalytic amounts of TiBn4 , Ph3 C[B(C6 F5 )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 promi ...[more]

PMID: 34936144

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