Easy kinetic resolution of some bêta-amino alcohols by Candida antarctica lipase B catalyzed hydrolysis in organic media

• Published in: Tetrahedron: Asymmetry
• Main Authors: Alalla, Affef, Merabet-Khelassi, Mounia, Riant, Olivier, Aribi-Zouioueche, Louisa
• Other Authors: UCL - SST/IMCN/MOST - Molecules, Solids and Reactivity
• Format: Article in Journal/Newspaper
• Language: English
• Published: Pergamon 2016
• Subjects: Antarc*; Antarctica
• Online Access: http://hdl.handle.net/2078.1/181204; https://doi.org/10.1016/j.tetasy.2016.10.003

Herein, we present an easy and eco-friendly pathway to obtain some enantiomerically enriched b-amino alcohols using essentially as b-blockers. The enzymatic hydrolysis is conducted in hydrophobic organicmedia, assisted by sodium carbonate and CAL-B. We describe a new and effective procedure in terms of the chemo- and enantioselectivity, which allows for the formation of both enantiomers: the 2-acetamido-1-arylacetates and 2-acetamido-1-arylethanols were obtained with high ee values (up to >99%), while the selectivities reached E >200. The obtained results show a high CAL-B affinity toward the deacylation of the 2-acetamido-1-arylacetates compared to the acylation one. The structure of the 2-acetamido-1-arylacetates had a significant influence on both reactivity and selectivity of the CAL-B catalyzed deacylation. A multigram scale O-deacylation of racemic 2-acetamido-1-phenylacetate has been carried out, giving access both enantiomers with high enantiomeric purity and good isolated chemical yields.