Hyppää sisältöön
    • Suomeksi
    • In English
Trepo
  • Suomeksi
  • In English
  • Kirjaudu
Näytä viite 
  •   Trepo etusivu
  • Trepo
  • Väitöskirjat
  • Näytä viite
  •   Trepo etusivu
  • Trepo
  • Väitöskirjat
  • Näytä viite
JavaScript is disabled for your browser. Some features of this site may not work without it.

Chiral Indole Ligands: Preparation and Application in Catalytic Asymmetric Allylic Substitutions

Wang, Yu (2012)

 
Tweet refworks
 
Avaa tiedosto
wang.pdf (4.199Mt)
Lataukset: 



Wang, Yu
Tampere University of Technology
2012

Luonnontieteiden ja ympäristötekniikan tiedekunta - Faculty of Science and Environmental Engineering
This publication is copyrighted. You may download, display and print it for Your own personal use. Commercial use is prohibited.
Näytä kaikki kuvailutiedot
Julkaisun pysyvä osoite on
http://urn.fi/URN:ISBN:978-952-15-2869-9
Tiivistelmä
Indoles have high structural flexibility, and the functionalization of the indole skeleton has extensively been investigated. Therefore various possibilities are offered for the design of catalytic ligands with an indole core. The theory part of this thesis is divided into three parts: the first part is an introduction on the use of chiral catalytic ligands with focus on oxazoline-containing ligands; the second part introduces the modification of the indole ring system at the N1-, C2- and C3-position; the third part gives an overall introduction on catalytic asymmetric allylic substitution with hetero-nucleophiles. In the results part of the thesis, the design and preparation of novel indole-phosphine-oxazoline (IndPHOX) ligands from readily available starting materials are presented. These modular ligands include an indole skeleton with either a phosphine moiety at the 2- or 3-position or an oxazoline ring at the 1-, 2- or 3-position, respectively.

The IndPHOX ligands were first evaluated in palladium-catalyzed allylic alkylation with dimethyl malonate, generating the product in good yield and high ee. The ligands with a diphenylphosphine group and an oxazoline moiety at the 2 or 3-position, respectively, demonstrated high catalytic efficiency in palladium-catalyzed allylic amination with various N-nucleophiles, even with aromatic aniline having low nucleophilicity. N-functionalized IndPHOX ligands bearing various groups were also synthesized. The effects of N1-substituents to the reaction rate, yield and asymmetric induction in palladium-catalyzed asymmetric allylic amination have been discussed. In addition, the enhancement of enantioselectivity due to the presence of an oxygen atom in ligands with a N-MOM or a N-THP group has been presented in the thesis.

Moreover, an IndPHOX ligand was utilized to afford 2-aryl substituted chromans with sterocontrol at C-2 via asymmetric allylic etherification using a novel synthetic route.
Kokoelmat
  • Väitöskirjat [4097]
Kalevantie 5
PL 617
33014 Tampereen yliopisto
oa[@]tuni.fi | Yhteydenotto | Tietosuoja | Saavutettavuusseloste
 

 

Selaa kokoelmaa

TekijätNimekkeetTiedekunta (2019 -)Tiedekunta (- 2018)Tutkinto-ohjelmat ja opintosuunnatAvainsanatJulkaisuajatKokoelmat

Omat tiedot

Kirjaudu sisäänRekisteröidy
Kalevantie 5
PL 617
33014 Tampereen yliopisto
oa[@]tuni.fi | Yhteydenotto | Tietosuoja | Saavutettavuusseloste