A base-free hydroxylaminolysis protocol promoted by ZnO in deep eutectic solvents

Liang, Xinjie; Lv, Bingqing; Sun, Shitao; Wu, Zhixuan; Lin, Bin; Bao, Xuefei; Chen, Guoliang

doi:10.1039/d3gc00485f

Green Chem.

2023

DOI: 10.1039/d3gc00485f

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A base-free hydroxylaminolysis protocol promoted by ZnO in deep eutectic solvents

Xinjie Liang

Bingqing Lv

Shitao Sun

et al.

Abstract: There are many protocols for the preparation of hydroxamic acids from their corresponding carboxylic esters or carboxylic acids, but as for ester precursors, strong bases are usually indispensable. Herein, an...

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Cited by 3 publications

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Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine

Jäger,

Nieger,

Rissanen

et al. 2023

Eur J Org Chem

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The assembly of enzymatic cascades and multi‐step reaction sequences represents an attractive alternative to traditional synthetic‐organic approaches. The biocatalytic reaction mediators offer not only mild conditions and permit the use of environmentally benign reagents, but the high compatibility of different enzymes promises more streamlined reaction setups. In this study, a triple‐enzymatic strategy was developed that enables the direct conversion of γ,δ‐unsaturated esters to N‐hydroxy‐γ‐lactame building blocks. Hereby, a lipase‐catalyzed hydroxylaminolysis generates hydroxamic acid intermediates that are subsequently aerobically activated by horseradish peroxidase and glucose oxidase to cyclize in an intramolecular nitroso ene reaction. Utilizing the hydroxylaminolysis/ene‐cyclization sequence for the preparation of an aza‐spirocyclic lactam, the multi‐enzymatic methodology was successfully employed in the synthesis of key intermediates en route to alkaloids of the Cephalotaxus family.

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Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine

Jäger,

Nieger,

Rissanen

et al. 2023

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Facile fabrication of reusable starch sponge with adjustable crosslinked networks for efficient nest-trap and in situ photodegrade methylene blue

Gao,

Zhang,

Dong

et al. 2023

Carbohydrate Polymers

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Pyro-assisted deep eutectic solvents pretreatment of lignocellulosic biomass: A review

Yuan,

Li,

Huang

et al. 2024

Industrial Crops and Products

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A base-free hydroxylaminolysis protocol promoted by ZnO in deep eutectic solvents

Abstract: There are many protocols for the preparation of hydroxamic acids from their corresponding carboxylic esters or carboxylic acids, but as for ester precursors, strong bases are usually indispensable. Herein, an...

Cited by 3 publications

References 37 publications

Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine

Multienzymatic Synthesis of γ‐Lactam Building Blocks from Unsaturated Esters and Hydroxylamine

Facile fabrication of reusable starch sponge with adjustable crosslinked networks for efficient nest-trap and in situ photodegrade methylene blue

Pyro-assisted deep eutectic solvents pretreatment of lignocellulosic biomass: A review

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