Enzymatic Kinetic Resolution of Secondary Alcohols Using an Ionic Anhydride Generated In Situ

• Published in: ChemSusChem
• Main Authors: Rocha, Ângelo, Teixeira, Raquel, Lourenço, Nuno M. T., Afonso, Carlos A. M.
• Other Authors: Fundação para a Ciência e a Tecnologia (FCT)
• Format: Article in Journal/Newspaper
• Language: English
• Published: Wiley 2016
• Subjects: Antarc*; Antarctica
• Online Access: http://dx.doi.org/10.1002/cssc.201600579; https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fcssc.201600579; http://onlinelibrary.wiley.com/wol1/doi/10.1002/cssc.201600579/fullpdf

Abstract We developed a method for the resolution of secondary alcohols using an ionic anhydride acylating agent prepared directly in the reaction medium containing the biocatalyst Candida antarctica lipase B (CALB). NMR studies showed that mixing all components at the same time does not interfere with the coupling reaction or the enzymatic activity. After optimization of the reaction conditions, the method allowed the resolution of a number of substrates in very high conversions (46–48 %) and enantiomeric ratios ( E >170) along with an easy recovery of both enantiomers without the need for preparative chromatographic separation. Additionally, both the starting ionic acid and the biocatalyst could be recovered and reused up to nine cycles without significant loss of enantioselectivity.