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Open AccessArticle

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
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Molecules 2014, 19(9), 14273-14291; https://doi.org/10.3390/molecules190914273
Received: 15 July 2014 / Revised: 26 August 2014 / Accepted: 27 August 2014 / Published: 11 September 2014
(This article belongs to the Section Organic Chemistry)
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
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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.

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