'Watching' lipase-catalyzed acylations using 1H NMR: Competing hydrolysis of vinyl acetate in dry organic solvents

Hedda K. Weber, Hansjörg Weber, Romas J. Kazlauskas

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

Lipase-catalyzed acetylations of 1-phenylethanol with vinyl acetate were monitored in situ by 1H NMR spectroscopy. Surprisingly, even under dry conditions (no added water) the major reaction was hydrolysis of the vinyl acetate, not acetylation of the substrate. Because this competing hydrolysis consumes water and releases acetic acid, the reaction conditions in lipase-catalyzed acylations are not constant, but vary with the reaction time. Addition of a chiral shift reagent reveals the enantiomeric purity of the starting alcohol and allows calculation of the enantiomeric ratio, E, for the reaction.

Original languageEnglish (US)
Pages (from-to)2635-2638
Number of pages4
JournalTetrahedron Asymmetry
Volume10
Issue number14
DOIs
StatePublished - Jul 16 1999

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