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Stereoselective Synthesis of Tertiary Allylic Amines by Titanium‐Catalyzed Hydroaminoalkylation of Alkynes with Tertiary Amines
Author(s) -
Kaper Tobias,
Geik Dennis,
Fornfeist Felix,
Schmidtmann Marc,
Doye Sven
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202103931
Subject(s) - allylic rearrangement , stereoselectivity , trimethylamine , steric effects , chemistry , catalysis , tertiary amine , ligand (biochemistry) , substrate (aquarium) , titanium , intermolecular force , combinatorial chemistry , organic chemistry , medicinal chemistry , stereochemistry , molecule , biochemistry , oceanography , receptor , geology
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.