Coupling biocatalysis with high-energy flow reactions for the synthesis of carbamates and β-amino acid derivatives
- Alexander Leslie1
- Thomas S. Moody2,3
- Megan Smyth2
- Scott Wharry2
- Marcus Baumann1
- 1School of Chemistry, University College Dublin, D04 N2E2, Ireland
- 2Almac Group Ltd., Craigavon BT63 5QD, United Kingdom
- 3Arran Chemical Company, Athlone, Co. Roscommon N37 DN24, IrelandRead the publication that featured this abstract
A continuous flow process is presented that couples a Curtius rearrangement step with a biocatalytic impurity tagging strategy to produce a series of valuable Cbz-carbamate products. Immobilized CALB was exploited as a robust hydrolase to transform residual benzyl alcohol into easily separable benzyl butyrate. The resulting telescoped flow process was effectively applied across a series of acid substrates rendering the desired carbamate structures in high yield and purity. The derivatization of these products via complementary flow-based Michael addition reactions furthermore demonstrated the creation of β-amino acid species. This strategy thus highlights the applicability of this work towards the creation of important chemical building blocks for the pharmaceutical and speciality chemical industries.
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