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

The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid—1-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.