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Access to optically pure ?-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst.

ABSTRACT: The development of new approaches to obtain optically pure ?-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 ?-hydroxy esters using a planar-chiral DMAP derivative catalyst is presented. Following this procedure, a range of aromatic ?-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.

SUBMITTER: Diaz-Alvarez AE

PROVIDER: S-EPMC6270874 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Access to optically pure β-hydroxy esters via non-enzymatic kinetic resolution by a planar-chiral DMAP catalyst.

Díaz-Álvarez Alba E AE Mesas-Sánchez Laura L Dinér Peter P

Molecules (Basel, Switzerland) 20140911 9

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 ...[more]

PMID: 25215586

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