Aziridine and Oxirane Ring Openings “On Water”

Abstract

1) Li, C.-J.; Chan, T.-H. Organic reactions in aqueous media; Wiley: New York, 1997. 2) Grieco, P. A., Ed. Organic Synthesis in Water; Blackie: London,1998 3) Chanda, A.; Fokin, V. V. Chem. Rev. 2009, 109, 725. 4) Butler, R. N.; Coyne, A. G. Chem. Rev. 2010, 110, 6302. 5) Jung, Y.; Marcus, R. A. J. Am. Chem. Soc. 2007, 129, 5492. Future work Obtain SN1/SN2 selectivities for a series of epoxides to compare catalytic activity of water to conventional Lewis acids Explore compatibility of on water catalytic system in cascade reactions Conclusion Epoxide ring opening can be catalyzed by the surface of water “On water” methodology is applicable to aziridine opening The “on water” reactions afford higher yields than homogenous conditions “On water” conditions furnish clean products and minimize purification efforts Our methodology is compatible with diverse nitrogen and sulfur nucleophiles The Most Abundant Substance on Earth Non-Toxic & Non-Flammable High Boiling Point