Synthesis of Isothiocineole and Application in Multigram-Scale Sulfur Ylide Mediated Asymmetric Epoxidation and Aziridination

Martin P.Ó. Fearraigh, Johnathan V. Matlock, Ona Illa, Eoghan M. McGarrigle, Varinder K. Aggarwal

Research output: Contribution to journalArticleResearchpeer-review

4 Citations (Scopus)

Abstract

© 2018 Georg Thieme Verlag KG Stuttgart · New York. The synthesis of the chiral sulfide isothiocineole from limonene and elemental sulfur on multi-gram scale and its alkylation to make >50 g of the corresponding benzylsulfonium salt are described. The application of this salt to the sulfur ylide-mediated asymmetric epoxidation of aldehydes and the asymmetric aziridination of imines on a >5 g scale is demonstrated.
Original languageEnglish
Article numberss-2018-z0422-psp
Pages (from-to)3337-3343
JournalSynthesis (Germany)
Volume50
Issue number17
DOIs
Publication statusPublished - 1 Jan 2018

Keywords

  • asymmetric aziridination
  • asymmetric epoxidation
  • chiral sulfide
  • sulfur ylide

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