Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
| Autor: | Vladislav Vasilenko, Clemens K. Blasius, Niklas F. Heinrich, Lutz H. Gade |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
Asymmetric Reduction | Hot Paper
010402 general chemistry 01 natural sciences Catalysis imine reduction Metal chemistry.chemical_compound iron hydroboration Pincer ligand Alkyl chemistry.chemical_classification enantioselective catalysis Fendiline 010405 organic chemistry Chemistry Communication Enantioselective synthesis General Chemistry Isoindoline General Medicine Combinatorial chemistry Communications 0104 chemical sciences Hydroboration visual_art N-alkyl amines visual_art.visual_art_medium |
| Zdroj: | Angewandte Chemie (International Ed. in English) |
| ISSN: | 1521-3773 1433-7851 |
| Popis: | 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. Ironing imines: The first iron‐catalyzed asymmetric reduction of N‐alkyl imines is reported. A molecularly defined iron complex catalyzes the highly enantioselective hydroboration of various N‐alkyl imines, providing access to the corresponding α‐chiral amines in high yields and stereoselectivities. The earth‐abundant metal catalyst was applied in the synthesis of the pharmaceuticals Fendiline and Tecalcet. |
| Databáze: | OpenAIRE |
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