Minimizing side reactions in chemoenzymatic dynamic kinetic resolution: organometallic and material strategies

Ciara L. Pollock, Kevin J. Fox, Sophie D. Lacroix, James McDonagh, Patricia C. Marr, Alanna M. Nethercott, Annie Pennycook, Shimeng Qian, Linda Robinson, Graham C. Saunders, Andrew C. Marr

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Abstract

Chemoenzymatic dynamic kinetic resolution (DKR) of rac-1-phenyl ethanol into R-1-phenylethanol acetate was investigated with emphasis on the minimization of side reactions. The organometallic hydrogen transfer (racemization) catalyst was varied, and this was observed to alter the rate and extent of oxidation of the alcohol to form ketone side products. The performance of highly active catalyst [(pentamethylcyclopentadienyl) IrCl2(1-benzyl,3-methyl-imidazol-2-ylidene)] was found to depend on the batch of lipase B used. The interaction between the bio- and chemo-catalysts was reduced by employing physical entrapment of the enzyme in silica using a sol-gel process. The nature of the gelation method was found to be important, with an alkaline method preferred, as an acidic method was found to initiate a further side reaction, the acid catalyzed dehydration of the secondary alcohol. The acidic gel was found to be a heterogeneous solid acid.
Original languageEnglish
Pages (from-to)13423-13428
Number of pages6
JournalDalton transactions (Cambridge, England : 2003)
Volume41
Issue number43
Early online date07 Sep 2012
DOIs
Publication statusPublished - 21 Nov 2012

ASJC Scopus subject areas

  • Inorganic Chemistry

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    Pollock, C. L., Fox, K. J., Lacroix, S. D., McDonagh, J., Marr, P. C., Nethercott, A. M., Pennycook, A., Qian, S., Robinson, L., Saunders, G. C., & Marr, A. C. (2012). Minimizing side reactions in chemoenzymatic dynamic kinetic resolution: organometallic and material strategies. Dalton transactions (Cambridge, England : 2003), 41(43), 13423-13428. https://doi.org/10.1039/c2dt31781h