Tackling N‐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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Autores principales: Blasius, Clemens K., Heinrich, Niklas F., Vasilenko, Vladislav, Gade, Lutz H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7539954/
https://www.ncbi.nlm.nih.gov/pubmed/32453491
http://dx.doi.org/10.1002/anie.202006557
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author Blasius, Clemens K.
Heinrich, Niklas F.
Vasilenko, Vladislav
Gade, Lutz H.
author_facet Blasius, Clemens K.
Heinrich, Niklas F.
Vasilenko, Vladislav
Gade, Lutz H.
author_sort Blasius, Clemens K.
collection PubMed
description 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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spelling pubmed-75399542020-10-09 Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines Blasius, Clemens K. Heinrich, Niklas F. Vasilenko, Vladislav Gade, Lutz H. Angew Chem Int Ed Engl Communications 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. John Wiley and Sons Inc. 2020-06-25 2020-09-07 /pmc/articles/PMC7539954/ /pubmed/32453491 http://dx.doi.org/10.1002/anie.202006557 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Blasius, Clemens K.
Heinrich, Niklas F.
Vasilenko, Vladislav
Gade, Lutz H.
Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
title Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
title_full Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
title_fullStr Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
title_full_unstemmed Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
title_short Tackling N‐Alkyl Imines with 3d Metal Catalysis: Highly Enantioselective Iron‐Catalyzed Synthesis of α‐Chiral Amines
title_sort tackling n‐alkyl imines with 3d metal catalysis: highly enantioselective iron‐catalyzed synthesis of α‐chiral amines
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7539954/
https://www.ncbi.nlm.nih.gov/pubmed/32453491
http://dx.doi.org/10.1002/anie.202006557
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