Issue 43, 2012
From the journal:

Dalton Transactions

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

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

* Corresponding authors

a School of Chemistry and Chemical Engineering, Queen's University Belfast, David Keir Building, Belfast, UK
E-mail: a.marr@qub.ac.uk

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.

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

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Article information

DOI
https://doi.org/10.1039/C2DT31781H
Article type
Paper
Submitted
03 Aug 2012
Accepted
06 Sep 2012
First published
07 Sep 2012
This article is Open Access

Dalton Trans., 2012,41, 13423-13428

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

C. L. Pollock, K. J. Fox, S. D. Lacroix, J. McDonagh, P. C. Marr, A. M. Nethercott, A. Pennycook, S. Qian, L. Robinson, G. C. Saunders and A. C. Marr, Dalton Trans., 2012, 41, 13423 DOI: 10.1039/C2DT31781H

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