Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Polymer-Bound Pyridine-Bis(oxazoline). Preparation through Click Chemistry and Evaluation in Asymmetric Catalysis
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.ORCID iD: 0000-0002-1743-7650
Laboratoire de Chimie Organique Fine et Hétérocyclique, UMR 6014, Université et INSA de Rouen.
2007 (English)In: Advanced Synthesis and Catalysis, ISSN 1615-4150, E-ISSN 1615-4169, Vol. 349, no 13, 2079-2084 p.Article in journal (Refereed) Published
Abstract [en]

A pyridine-bis(oxazoline) ligand was efficiently immobilized by copper(I)-catalyzed azide-alkyne cycloaddition onto a polystyrene resin. The so obtained click-pybox resin 1a was associated with various metal salts (YbCl3, LuCl3, CuOTf) and the resulting resin-bound catalysts were explored in ring-opening of cyclohexene oxide, silylcyanation of benzaldehyde and alkynylation of imines. These new polymer-supported catalysts exhibit good to excellent performances in terms of catalytic activity, enantioselectivity and recyclability.

Place, publisher, year, edition, pages
2007. Vol. 349, no 13, 2079-2084 p.
Keyword [en]
asymmetric catalysis, click chemistry, copper(I), immobilization, lanthanides, pybox
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-4886DOI: 10.1002/adsc.200700112ISI: 000249833300001Scopus ID: 2-s2.0-34948850749OAI: oai:DiVA.org:kth-4886DiVA: diva2:1768
Note
QC 20100914Available from: 2008-09-16 Created: 2008-09-16 Last updated: 2017-12-13Bibliographically approved
In thesis
1. Synthesis and study of new oxazoline-based ligands
Open this publication in new window or tab >>Synthesis and study of new oxazoline-based ligands
2008 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

This thesis deals with the study of oxazoline-based ligands in metal-catalyzed asymmetric reactions.

The first part describes the synthesis of six new bifunctinal pyridine-bis(oxazoline) ligands and their applications in asymmetric metal-catalysis. These ligands, in addition to a Lewis acid coordination site, are equipped with a Lewis basic part in the 4-position of the oxazoline rings. Dual activation by means of this system was probed in cyanide addition to aldehydes.

The second part is concerned with the synthesis of two pyridine-bis(oxazoline) ligands bearing bulky triazole groups in the 4-position of the oxazoline rings and a macrocyclic ligand consisting of a pyridine-bis(oxazoline) moiety and a diaza-18-crown-6 ether. The synthesis of these compounds benefits from the use of “click chemistry”. The ligands thus obtained were tested in different asymmetric catalytic reactions. Complexation studies with different bifunctional molecules that could bind into the cavity of the macrocycle were carried out using NMR spectroscopy.

A third chapter is devoted to the synthesis of a supported pyridine-bis(oxazoline) catalyst and its use in catalysis. The pyridine-bis(oxazoline) ligand was efficiently connected to a polystyrene resin via a robust triazole linker. This resin could be employed in different metal-catalyzed asymmetric reactions and good results were obtained in terms of yield and enantioselectivity. Moreover, this polymer-bound ligand could be easily and efficiently recycled.

Finally, the last part deals with the use of a hydroxy-containing phosphinooxazoline ligand in the hydrosilylation of imines and in the asymmetric intermolecular Heck reaction. A cationic iridium complex of this ligand was studied by NMR spectroscopy.

Place, publisher, year, edition, pages
Stockholm: KTH, 2008. 101 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2008:54
Keyword
organic chemistry
National Category
Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-4858 (URN)978-91-7415-093-3 (ISBN)
Public defence
2008-09-19, E3, Osquars Backe 14, KTH, 10:00 (English)
Opponent
Supervisors
Note
QC 20100914Available from: 2008-09-10 Created: 2008-09-04 Last updated: 2010-09-14Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full textScopus

Authority records BETA

Moberg, Christina

Search in DiVA

By author/editor
Tilliet, MélanieLundgren, StinaMoberg, Christina
By organisation
Organic Chemistry
In the same journal
Advanced Synthesis and Catalysis
Organic Chemistry

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 49 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf