Díaz-Álvarez Alba E, Mesas-Sánchez Laura, Dinér Peter
Department of Chemistry-BMC, Uppsala University, Box 576, Uppsala SE-75123, Sweden.
Molecules. 2014 Sep 11;19(9):14273-91. doi: 10.3390/molecules190914273.
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.
开发获得光学纯β-羟基酯的新方法是合成有机化学中的一个重要领域，因为它们是其他高价值化合物的前体。本文介绍了使用平面手性DMAP衍生物催化剂对外消旋β-羟基酯进行动力学拆分。按照此方法，获得了一系列具有优异选择性（高达s = 107）和高对映体过量（高达99% ee）的芳香族β-羟基酯。此外，本方法的实用性在以对映体纯形式合成(S)-3-羟基-N-甲基-3-苯基丙酰胺中得到了证明，该化合物是生物活性分子如氟西汀、托莫西汀或尼索西汀的关键中间体。
