Iridium-Catalyzed Asymmetric Hydrogenation of 2,3-Diarylallyl Amines with a Threonine-Derived P-Stereogenic Ligand for the Synthesis of Tetrahydroquinolines and Tetrahydroisoquinolines
Rojo, Pep ; Molinari, Medea ; Cabré, Albert ; García-Mateos, Clara LU
; Riera, Antoni
and Verdaguer, Xavier
(2022)
In Angewandte Chemie - International Edition
61(29).
- 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... (More)
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.
(Less)
- author
- Rojo, Pep
; Molinari, Medea
; Cabré, Albert
; García-Mateos, Clara
LU
; Riera, Antoni
and Verdaguer, Xavier
- publishing date
- 2022-07-18
- type
- Contribution to journal
- publication status
- published
- keywords
- Allyl Amines, Asymmetric Hydrogenation, Iridium, P-Stereogenic, Tetrahydroquinolines
- in
- Angewandte Chemie - International Edition
- volume
- 61
- issue
- 29
- article number
- e2022043
- pages
- 6 pages
- publisher
- John Wiley & Sons Inc.
- external identifiers
-
- scopus:85130997987
- pmid:35543384
- ISSN
- 1433-7851
- DOI
- 10.1002/anie.202204300
- language
- English
- LU publication?
- no
- id
- dc3e49ad-7e50-4975-9a96-aa9fcd40b5b0
- date added to LUP
- 2023-11-22 15:44:58
- date last changed
- 2024-08-10 05:27:49
@article{dc3e49ad-7e50-4975-9a96-aa9fcd40b5b0,
abstract = {{<p>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.</p>}},
author = {{Rojo, Pep and Molinari, Medea and Cabré, Albert and García-Mateos, Clara and Riera, Antoni and Verdaguer, Xavier}},
issn = {{1433-7851}},
keywords = {{Allyl Amines; Asymmetric Hydrogenation; Iridium; P-Stereogenic; Tetrahydroquinolines}},
language = {{eng}},
month = {{07}},
number = {{29}},
publisher = {{John Wiley & Sons Inc.}},
series = {{Angewandte Chemie - International Edition}},
title = {{Iridium-Catalyzed Asymmetric Hydrogenation of 2,3-Diarylallyl Amines with a Threonine-Derived P-Stereogenic Ligand for the Synthesis of Tetrahydroquinolines and Tetrahydroisoquinolines}},
url = {{http://dx.doi.org/10.1002/anie.202204300}},
doi = {{10.1002/anie.202204300}},
volume = {{61}},
year = {{2022}},
}