Isothiourea-catalyzed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters
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A protocol for the isothiourea-catalysed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters using Hantzsch ester has been developed. Good to excellent yields are observed using α,β-unsaturated aryl esters bearing electron-withdrawing β-substituents. The aryl ester products can either be isolated directly in moderate to excellent yields (7 examples, 16–98%) or converted to the corresponding methyl esters (2 examples, 68–70% yield) or benzyl amides (2 examples, 44–88% yield) after in situ reaction of the hydrogenated ester with the appropriate nucleophile. Preliminary experiments showed that modest enantioinduction (76:24 er) is possible when a chiral isothiourea catalyst was used.
Wu , J , Young , C M & Smith , A D 2020 , ' Isothiourea-catalyzed transfer hydrogenation of α,β-unsaturated para -nitrophenyl esters ' , Tetrahedron , vol. In press , 131758 . https://doi.org/10.1016/j.tet.2020.131758
Copyright © 2020 Elsevier Ltd. All rights reserved. This work has been made available online in accordance with publisher policies or with permission. Permission for further reuse of this content should be sought from the publisher or the rights holder. This is the author created accepted manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tet.2020.131758
DescriptionThe research leading to these results (JW) has received funding from the ERC under the European Union's Seventh Framework Programme (FP7/2007–2013)/ERC grant agreement no 279850. ADS thanks the Royal Society for a Wolfson Research Merit Award.
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