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

Martin Fearraigh, Johnathan Matlock, Ona Illa Soler, Eoghan M. McGarrigle, Varinder Aggarwal

Research output: Contribution to journalArticle (Academic Journal)peer-review

4 Citations (Scopus)
152 Downloads (Pure)

Abstract

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
Pages (from-to)3337-3343
Number of pages7
JournalSynthesis (Germany)
Volume50
Issue number17
Early online date19 Jul 2018
DOIs
Publication statusPublished - 1 Sep 2018

Structured keywords

  • BCS and TECS CDTs

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