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

• 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.

Ämnesord

NATURVETENSKAP  -- Kemi -- Organisk kemi (hsv//swe)

NATURAL SCIENCES  -- Chemical Sciences -- Organic Chemistry (hsv//eng)

Nyckelord

lipase

hindered alcohol

hemiacetal ester

Organic chemistry

Organisk kemi

Publikations- och innehållstyp

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art (ämneskategori)