✦ LIBER ✦

Formation of hemiacetal esters in lipase-catalysed reactions of vinyl esters with hindered secondary alcohols

✍ Scribed by Hans-Erik Högberg; Marica Lindmark; Dan Isaksson; Kristina Sjödin; Maurice C.R. Franssen *; Hugo Jongejan; Joannes B.P.A. Wijnberg; Aede de Groot

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 175 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00328-2

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✦ Synopsis

Normally many lipases are efficient catalysts for the acetylation of alcohols with vinyl acetate. Unexpectedly, we found that some sterically hindered secondary alcohols react slowly to yield hemiacetal esters as mixtures of diastereomers. Their formation can be explained by the reaction of the alcohol with acetaldehyde that is produced by the lipase-catalysed splitting of vinyl acetate and subsequent acetylation of the resulting hemiacetal by the lipase.

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