Abstract

From Waste to Value—Direct Utilization of α-Angelica Lactone as a Nonconventional Irreversible Acylating Agent in a Chromatography-Free Lipase-Catalyzed KR Approach toward <i>sec</i>-Alcohols

Highlights

  • Classical enzymatic kinetic resolution (EKR) relies on a simple and well-known phenomenon that due to the chirality of the active site of the enzyme, one enantiomer fits better into the active site than its counterpart and is converted at a higher rate.[1]

  • Platform chemicals such as levulinic acid (LA) have gained much attention due to their attractive properties and the possibility to be further converted into highly desirable building blocks useful in the synthesis of specialty chemicals,[30−34] functional materials,[35] as well as biopolymers[36−40] and biofuels.[41−45] enormous interest in LA stems from its availability and low cost as this key carboxylic acid is obtainable from renewable feedstock, being the product of bioremediation and valorization of lignocellulosic biomass and further direct functionalization of

  • Among LA-derived compounds (i) alkyl levulinates (LAE), (ii) α-angelica lactone (α-AL) [and its isomers: 5-methylenedihydrofuran-2(3H)-one (α-methylene-γ-valerolactone known as α′-angelica lactone, α′-AL) and 5-methyl-2(5H)-furanone], as well as (iii) γ-valerolactone (GVL), γ-aminolevulinic acid (ALA), and methyl vinyl ketone (MVK) deserve considerable attention as synthetic building blocks.[51,52]

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Summary

■ INTRODUCTION

Classical enzymatic kinetic resolution (EKR) relies on a simple and well-known phenomenon that due to the chirality of the active site of the enzyme, one enantiomer fits better into the active site than its counterpart and is converted at a higher rate.[1]. The copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) applied therein to obtain acid-washable ester derivative requires the use of organic azides, which are classified as highly explosive and toxic reagents To avoid both aqueous basic and acidic extractive-separation workup, “neutral” selective LLEs have been developed using acyl donors designed on the basis of 1,ω-dicarboxylated poly(ethylene glycol) (PEG600-dicarboxylate diethyl esters),[21] an in situ generated ionic anhydrides,[22,23] task-specific ionic liquids (TSILs),[24] and/or fluorous esters[25,26] (Figure 2). Scheme 1. α-Angelica Lactone as Irreversible Acyl Donor for Enantioselective Enzymatic Acylations

■ RESULTS AND DISCUSSION
■ CONCLUSIONS
■ ACKNOWLEDGMENTS
■ REFERENCES

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