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Títol: Towards chiral 3-phenyl-tetrahydroquinolines through iridium catalyzed asymmetric hydrogenation
Altres títols: Envers 3-fenil-tetrahidroquinolines quirals mitjançant hidrogenació asimètrica catalitzada per iridi
Autor: García Mateos, Clara
Director/Tutor: Verdaguer i Espaulella, Xavier
Rojo Solé, Josep Maria
Matèria: Hidrogenació asimètrica
Iridi
Fosfinooxazolines
Treballs de fi de grau
Asymmetric hydrogenation
Iridium
Phosphinooxazolines
Bachelor's theses
Data de publicació: 2021
Resum: Asymmetric catalysis has had an impact over more than half a century, due to the fact that it is one of the most efficient methods to prepare chiral organic compounds. When it comes to asymmetric hydrogenation, Pfaltz demonstrated that introducing iridium as the metal centre in phosphinooxazolines ligands was very efficient, especially with a bulky non-coordinating anion such as BArF. Inspired by this, our group has been working on a new catalyst, Ir-(S)P-DTP, whose structure bears a phosphinooxazoline ligand derived from threonine, in which a P-stereogenic centre has been introduced in order to increase the performance of the catalyst. This new catalyst has shown excellent conversion and enantiomeric excess for β,γ-substituted allylic carbamates. In this project, allylic carbamates have been synthesized and submitted to asymmetric hydrogenation with the Ir-(S)P-DTP catalyst to extend the scope. Two of have provided total conversion and excellent enantiomeric excess. An allylic carbamate with an ortho-chloride in the terminal phenyl ring has also been synthesized and submitted to asymmetric hydrogenation, providing successful results as well. Additionally, the compound with an ortho-chloride has been tested in the intramolecular Buchwald-Hartwig reaction to yield the corresponding chiral 3-phenyl-tetrahydroquinoline
Nota: Treballs Finals de Grau de Química, Facultat de Química, Universitat de Barcelona, Any: 2021, Tutors: Xavier Verdaguer Espaulella, Pep Rojo Solé
URI: https://hdl.handle.net/2445/179923
Apareix en les col·leccions:Treballs Finals de Grau (TFG) - Química

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