Next Article in Journal
On the Nature of the Transition State Characterizing Gated Molecular Encapsulations
Previous Article in Journal
Two New Guaiane Sesquiterpenoids from Daphne holosericea (Diels) Hamaya
Article Menu

Export Article

Open AccessArticle
Molecules 2014, 19(9), 14273-14291; doi:10.3390/molecules190914273

Access to Optically Pure β-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst

1
Department of Chemistry-BMC, Uppsala University, Box 576, Uppsala SE-75123, Sweden
2
Department of Chemistry-Organic Chemistry, KTH Royal Institute of Technology, Stockholm SE-100 44, Sweden
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 15 July 2014 / Revised: 26 August 2014 / Accepted: 27 August 2014 / Published: 11 September 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [952 KB, uploaded 11 September 2014]   |  

Abstract

The development of new approaches to obtain optically pure β-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 β-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic β-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. View Full-Text
Keywords: non-enzymatic kinetic resolution; β-hydroxy esters; planar-chiral DMAP catalyst; ferrocenyl catalyst non-enzymatic kinetic resolution; β-hydroxy esters; planar-chiral DMAP catalyst; ferrocenyl catalyst
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Supplementary material

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Díazlvarez, A.E.; Mesas-Sánchez, L.; Dinér, P. Access to Optically Pure β-Hydroxy Esters via Non-Enzymatic Kinetic Resolution by a Planar-Chiral DMAP Catalyst. Molecules 2014, 19, 14273-14291.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top