Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 1013-1018
doi:10.1351/pac200880051013
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.
Keywords: 1,3-dipolar cycloadditions; asymmetric reactions; Lewis acids; nitrile oxides; nitrones.
*Paper based on a presentation at the 14th International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-14), 2-6 August 2007, Nara, Japan. Other presentations are published in this issue, pp. 807-1194.
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