Biocatalyzed synthesis of enantiomerically enriched β-5-like dimer of 4-vinylphenol

The tandem use of laccases and lipases has been exploited for the preparative scale synthesis of enantiomerically enriched dimeric phenols.Laccase-catalyzed oxidation of 4-vinylphenol (3) in biphasic systems gave as main product the racemic compound 4.The enantiomerically enriched butanoate (+)-4b and acetate (−)-4a could be obtained by alcoholysis reactions catalyzed by porcine pancreatic lipase in organic solvent and subsequent acetylation.

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► Preparative scale synthesis of enantiomerically enriched dimeric phenols has been achieved by tandem use of laccases and lipases.
► Racemic compound 4 was the main product of laccase-catalyzed oxidation of 4-vinylphenol (3).
► Alcoholysis reactions catalyzed by porcine pancreatic lipase in organic solvent, followed by acetylation, gave the enantiomerically enriched butanoate (+)-4b and acetate (−)-4a.