Tackling a-Alkyl imines with 3d metal catalysis: highly enantioselective iron-catalyzed synthesis of α-chiral amines

A readily activated iron alkyl precatalyst effectively catalyzes the highly enantioselective hydroboration of N-alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N-alkyl imines provided the corresponding α-chiral amines...

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Hauptverfasser: Blasius, Clemens K. (VerfasserIn) , Heinrich, Niklas (VerfasserIn) , Vasilenko, Vladislav (VerfasserIn) , Gade, Lutz H. (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2020
In: Angewandte Chemie
Year: 2020, Jahrgang: 132, Heft: 37, Pages: 16108-16111
ISSN:1521-3757
DOI:10.1002/ange.202006557
Online-Zugang:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/ange.202006557
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ange.202006557
Volltext
Verfasserangaben:Clemens K. Blasius, Niklas F. Heinrich, Vladislav Vasilenko, and Lutz H. Gade

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520 |a A readily activated iron alkyl precatalyst effectively catalyzes the highly enantioselective hydroboration of N-alkyl imines. Employing a chiral bis(oxazolinylmethylidene)isoindoline pincer ligand, the asymmetric reduction of various acyclic N-alkyl imines provided the corresponding α-chiral amines in excellent yields and with up to >99 % ee. The applicability of this base metal catalytic system was further demonstrated with the synthesis of the pharmaceuticals Fendiline and Tecalcet. 
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