Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • 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
Synthesis and Screening of C-1-Substituted Tetrahydroisoquinoline Derivatives for Asymmetric Transfer Hydrogenation Reactions
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
Show others and affiliations
2010 (English)In: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, no 5, p. 972-980Article in journal (Refereed) Published
Abstract [en]

Tetrahydroisoquinoline (TIQ) derivatives exhibit good biological activity. However, utilization of TIQ compounds in asymmetric catalysis is limited. This paper presents a series of TIQ derivatives in asymmetric transfer hydrogenation (ATH) reactions. Chiral TIQ amino alcohol ligands were synthesized and screened for the ATH reaction of aromatic ketones. The effect of a cis- and trans-phenyl substitution at the C-1 position on the ligand backbone was investigated both experimentally and computationally. The results showed that the trans orientation on the TIQ scaffold yields higher turnover rates with a selectivity of 94% ee obtained at room temperature with an Ru complex. The cis isomer results in a high turnover rate with no selectivity. The trans isomer gave 99% ee at lower temperatures. Furthermore, it was observed that substitution at the C-3-alpha position results in a drop of the enantioselectivity and the reactivity of the catalyst.

Place, publisher, year, edition, pages
2010. no 5, p. 972-980
Keywords [en]
Tetrahydroisoquinoline, Amino alcohols, Ruthenium, Hydrogenation, Asymmetric catalysis
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-137267DOI: 10.1002/ejoc.200901159ISI: 000274843100021OAI: oai:DiVA.org:uu-137267DiVA, id: diva2:377998
Available from: 2010-12-15 Created: 2010-12-15 Last updated: 2017-12-11Bibliographically approved

Open Access in DiVA

fulltext(1044 kB)136 downloads
File information
File name FULLTEXT01.pdfFile size 1044 kBChecksum SHA-512
16f4562691dea9aef94383f9055a54d28402c2f2751ec870f6afa1239d71b4929f5be203ea646db0e9ce93c0a112cf01215803c8dc8438329d374bb4ce6d204e
Type fulltextMimetype application/pdf

Other links

Publisher's full text

Search in DiVA

By author/editor
Andersson, Pher G
By organisation
Department of Biochemistry and Organic Chemistry
In the same journal
European Journal of Organic Chemistry
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar
Total: 136 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 497 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • 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