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

M Namutebi, EM McGarrigle…

Index: Namutebi, Mariam; McGarrigle, Eoghan M.; Aggarwal, Varinder K. Phosphorus, Sulfur and Silicon and the Related Elements, 2010 , vol. 185, # 5-6 p. 1250 - 1272

Full Text: HTML

Citation Number: 1

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 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 (er 85: 15, trans: cis 90: 10, 87% yield). The amino group ...