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

      Pollock, Ciara L.; Fox, Kevin J.; Lacroix, Sophie D.; McDonagh, James; Marr, Patricia C.; Nethercott, Alanna M.; Pennycook, Annie; Qian, Shimeng; Robinson, Linda; Saunders, Graham C.; Marr, Andrew C.
      DOI
       10.1039/c2dt31781h
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      Pollock, C. L., Fox, K. J., Lacroix, S. D., McDonagh, J., Marr, P. C., Nethercott, A. M., Pennycook, A., et al. (2012). Minimizing side reactions in chemoenzymatic dynamic kinetic resolution: organometallic and material strategies. Dalton Transactions, 41(43), 13423-13428.
      Permanent Research Commons link: https://hdl.handle.net/10289/6873
      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.
      Date
      2012
      Type
      Journal Article
      Publisher
      Royal Society of Chemistry
      Collections
      • Science and Engineering Papers [3019]
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