Isothiourea-Catalysed Acylative Kinetic Resolution of Aryl–Alkenyl (sp2vs. sp2) Substituted Secondary Alcohols

Stefania F. Musolino, O. Stephen Ojo, Nicholas J. Westwood, James E. Taylor, Andrew D. Smith

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

The non-enzymatic acylative kinetic resolution of challenging aryl–alkenyl (sp2vs. sp2) substituted secondary alcohols is described, with effective enantiodiscrimination achieved using the isothiourea organocatalyst HyperBTM (1 mol %) and isobutyric anhydride. The kinetic resolution of a wide range of aryl–alkenyl substituted alcohols has been evaluated, with either electron-rich or naphthyl aryl substituents in combination with an unsubstituted vinyl substituent providing the highest selectivity (S=2–1980). The use of this protocol for the gram-scale (2.5 g) kinetic resolution of a model aryl–vinyl (sp2vs. sp2) substituted secondary alcohol is demonstrated, giving access to >1 g of each of the product enantiomers both in 99:1 e.r.

Original languageEnglish
Pages (from-to)18916-18922
Number of pages7
JournalChemistry - A European Journal
Volume22
Issue number52
Early online date30 Nov 2016
DOIs
Publication statusPublished - 21 Dec 2016

Keywords

  • acylation
  • isothiourea
  • kinetic resolution
  • organocatalysis
  • renewable resources

ASJC Scopus subject areas

  • Chemistry(all)

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