Isothiourea-catalyzed transfer hydrogenation of α,β-unsaturated para-nitrophenyl esters

Jiufeng Wu, Claire Mary Young, Andrew David Smith*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
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Abstract

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.
Original languageEnglish
Article number131758
JournalTetrahedron
VolumeIn press
Early online date13 Nov 2020
DOIs
Publication statusE-pub ahead of print - 13 Nov 2020

Keywords

  • Transfer hydrogenation
  • Isothiourea
  • Organocatalysis
  • Hantzsch ester

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