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

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 diiso...

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Published inCatalysis letters Vol. 145; no. 3; pp. 919 - 929
Main Authors Kumar, Gaurav, Dhawan, Ashish, Singh, Brajendra K., Sharma, Nawal K., Sharma, Sunil K., Prasad, Ashok K., Van der Eycken, Erik V., Len, Christophe, Watterson, Arthur C., Parmar, Virinder S.
Format Journal Article
LanguageEnglish
Published Boston Springer US 01.03.2015
Springer
Springer Nature B.V
Subjects
Acidic oxides
Acylation
Anhydrides
Aromatic compounds
Biocatalysts
Catalysis
Chemistry
Chemistry and Materials Science
Diesters
Hydroxyl groups
Industrial Chemistry/Chemical Engineering
Organometallic Chemistry
Physical Chemistry
Transesterification
Regioselectivity
Lipozyme
Deacylation
Aryl 3-hydroxy-2-(hydroxymethyl)-2-methylpropanoates
Lipase
TL IM
Acylation
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Summary: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. Graphical Abstract
ISSN:1011-372X
1572-879X
DOI:10.1007/s10562-014-1447-6