Application of Deep Eutectic Solvents in Promiscuous Lipase-Catalysed Aldol Reactions

Abstract

The application of deep eutectic solvents has been demonstrated for the first time in promiscuous lipase-catalysed aldol reactions. The model reaction between 4-nitrobenzaldehyde and acetone was examined in depth, with excellent compatibility being found between porcine pancreas lipase and choline chloride/glycerol mixtures for the formation of the aldol product in high yields. The system was compatible with a series of aromatic aldehydes and ketones including acetone, cyclopentanone and cyclohexanone. In some cases, the corresponding α,β-unsaturated carbonyl compounds were found as minor products. Control experiments demonstrate that the enzymatic preparation was also responsible for a collateral dehydration reaction once the aldol product is formed.

Deep eutectic solvents are used for the first time in promiscuous lipase-catalysed aldol reactions. The reaction between substituted benzaldehydes and aliphatic ketones has excellent compatibility with porcine pancreas lipase (PPL) and choline chloride/glycerol mixtures and gives the aldol product in high yields. PPL was also responsible for a collateral dehydration reaction.

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