Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes

Mariam Namutebi, Eoghan M. McGarrigle, Varinder K. Aggarwal*

*Corresponding author for this work

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

2 Citations (Scopus)

Abstract

The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.

Original languageEnglish
Article number922590300
Pages (from-to)1250-1272
Number of pages23
JournalPhosphorus, Sulfur, and Silicon and the Related Elements
Volume185
Issue number5-6
DOIs
Publication statusPublished - 2010

Keywords

  • Aziridine ring-opening
  • asymmetric epoxidation
  • ionic liquids
  • sulfide
  • sulfur ylide
  • thiols
  • YLIDE-MEDIATED EPOXIDATION
  • DIELS-ALDER REACTION
  • ENANTIOSELECTIVE SYNTHESIS
  • TRANSFER HYDROGENATION
  • CARBONYL-COMPOUNDS
  • CHIRAL AUXILIARY
  • SULFUR YLIDES
  • EPOXIDES
  • DERIVATIVES
  • REDUCTION

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