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Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1013-1018

Asymmetric Lewis acid-catalyzed 1,3-dipolar cycloadditions

Andrei Bădoiu, Yasmin Brinkmann, Florian Viton and E. Peter Kündig

Department of Organic Chemistry, University of Geneva, Sciences II,30 quai Ernest Ansermet, CH-1211 Geneva 4, Switzerland

Abstract: Highly tuned, one-point binding chiral iron and ruthenium complexes selectively coordinate and activate α,β-unsaturated aldehydes and ketones toward asymmetric catalytic Diels-Alder cycloaddition reactions. Here we focus on the application of these transition-metal Lewis acids to asymmetric catalytic 1,3-dipolar cycloaddition reaction between enals and cyclic and acyclic nitrones as well as aryl nitrile oxides to give isoxazolidines and isoxazolines, respectively.