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Highly Selective Biocatalytic Transesterification Reactions on Aryl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoates

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Abstract

Acid anhydrides have been used to carry out the regioselective acylation of primary hydroxyl group in benzyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate and 4-fluorobenzyl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoate and deacylation of their diesters in the presence of Lipozyme® TL IM in diisopropyl ether. Amongst different acid anhydrides used, butanoic anhydride was found to be the best acylating agent as compared to others. Both acylation and deacylation reactions were highly selective and efficient yielding exclusively the monoacylated products in 70–88 % yields.

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Acknowledgments

We thank the Polytechnic University (NYU-Poly, New York, USA), the University of Massachusetts Lowell (UML, USA), the Department of Biotechnology (DBT, Govt. of India, New Delhi), the University of Leuven (Belgium) and the University of Delhi (India) for financial assistance. VSP and BKS were supported by Grants from the EU under its Erasmus Mundus EMA 2 Program.

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Correspondence to Virinder S. Parmar.

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Dedicated with affection to our Friend and Collaborator, Professor Kalle Levon (NYU Polytechnic School of Engineering, Brooklyn, New York, USA) in commemoration of the completion of his 26 years in active research.

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Kumar, G., Dhawan, A., Singh, B.K. et al. Highly Selective Biocatalytic Transesterification Reactions on Aryl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoates. Catal Lett 145, 919–929 (2015). https://doi.org/10.1007/s10562-014-1447-6

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