Hydrazide-catalyzed 1,3-dipolar nitrone cycloadditions

Mathieu Lemay, University of Ottawa
John Trant, University of Ottawa
William W. Ogilvie, University of Ottawa


The triflate salts of cyclic hydrazides function as asymmetric catalysts for the [3+2]cycloadditions of nitrones with α,β-unsaturated aldehydes. The camphor-derived hydrazides show a preference for the exo isomers during these reactions, providing a compliment to other organically catalyzed dipolar cycloadditions. Enantiomeric excesses as high as 93% were realized for the exo isomers, while some endo products were obtained in 94% ee. © 2007 Elsevier Ltd. All rights reserved.