Mariam Namutebi, E. McGarrigle, V. Aggarwal
May 27, 2010
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Influential Citations
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Journal
Phosphorus, Sulfur, and Silicon and the Related Elements
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 (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.