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
Access to Optically Pure beta-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry. Uppsala University, Sweden.ORCID iD: 0000-0001-6782-6622
2014 (English)In: Molecules, ISSN 1420-3049, E-ISSN 1420-3049, Vol. 19, no 9, p. 14273-14291Article in journal (Refereed) Published
Abstract [en]

The development of new approaches to obtain optically pure beta-hydroxy esters is an important area in synthetic organic chemistry since they are precursors of other high value compounds. Herein, the kinetic resolution of racemic beta-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic beta-hydroxy esters was obtained in excellent selectivities (up to s = 107) and high enantiomeric excess (up to 99% ee). Furthermore, the utility of the present method was demonstrated in the synthesis of (S)-3-hydroxy-N-methyl-3-phenylpropanamide, a key intermediate for bioactive molecules such as fluoxetine, tomoxetine or nisoxetine, in its enantiomerically pure form.

Place, publisher, year, edition, pages
2014. Vol. 19, no 9, p. 14273-14291
Keywords [en]
non-enzymatic kinetic resolution, beta-hydroxy esters, planar-chiral DMAP catalyst, ferrocenyl catalyst
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-155805DOI: 10.3390/molecules190914273ISI: 000343093100085Scopus ID: 2-s2.0-84907092007OAI: oai:DiVA.org:kth-155805DiVA, id: diva2:763049
Funder
Swedish Research CouncilCarl Tryggers foundation
Note

QC 20141113

Available from: 2014-11-13 Created: 2014-11-13 Last updated: 2017-12-05Bibliographically approved

Open Access in DiVA

No full text in DiVA

Other links

Publisher's full textScopus

Authority records BETA

Dinér, Peter

Search in DiVA

By author/editor
Dinér, Peter
By organisation
Organic Chemistry
In the same journal
Molecules
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 25 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