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Tackling N-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of ?-Chiral Amines.

ABSTRACT: 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 ?-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.

SUBMITTER: Blasius CK

PROVIDER: S-EPMC7539954 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Tackling N-Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron-Catalyzed Synthesis of α-Chiral Amines.

Blasius Clemens K CK Heinrich Niklas F NF Vasilenko Vladislav V Gade Lutz H LH

Angewandte Chemie (International ed. in English) 20200625 37

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. ...[more]

PMID: 32453491

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