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

作者：Diaz Alvarez Alba E; Mesas Sanchez Laura; Diner Peter^*

来源：Molecules, 2014, 19(9): 14273-14291.

DOI：10.3390/molecules190914273

• non-enzymatic kinetic resolution
• beta-hydroxy esters
• planar-chiral DMAP catalyst
• ferrocenyl catalyst

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.

• 出版日期2014-9