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Title: Iridium-catalyzed asymmetric hydrogenation of 2,3-diarylallyl amines with a threonine-derived P-stereogenic ligand for the synthesis of tetrahydroquinolines and tetrahydroisoquinolines
Author: Rojo, Pep
Molinari, Medea
Cabré, Albert
García-Mateos, Clara
Riera i Escalé, Antoni
Verdaguer i Espaulella, Xavier
Keywords: Iridi
Issue Date: 11-May-2022
Publisher: Wiley-VCH
Abstract: Chiral compounds containing nitrogen heteroatoms are fundamental substances for the chemical, pharmaceutical and agrochemical industries. However, the preparation of some of these interesting scaffolds is still underdeveloped. Herein we present the synthesis of a family of P-stereogenic phosphinooxazoline iridium catalysts from L-threonine methyl ester and their use in the asymmetric hydrogenation of N-Boc-2,3-diarylallyl amines, achieving very high enantioselectivity. Furthermore, the synthetic utility of the 2,3-diarylpropyl amines obtained is demonstrated by their transformation to 3-aryl-tetrahydroquinolines and 4-benzyl-tetrahydroisoquinolines, which have not yet been obtained in an enantioselective manner by direct reduction of the corresponding aromatic heterocycles. This strategy allows the preparation of these types of alkaloids with the highest enantioselectivity reported up to date.
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It is part of: Angewandte Chemie-International Edition, 2022, vol. 61, num. 29, p. 1-6
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ISSN: 1433-7851
Appears in Collections:Articles publicats en revistes (Química Inorgànica i Orgànica)

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