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  • Title: Highly trans-stereoselective synthesis of bicyclic isoxazolidines via copper-catalyzed triple cascade catalysis.
    Author: Chen H, Wang Z, Zhang Y, Huang Y.
    Journal: J Org Chem; 2013 Apr 05; 78(7):3503-9. PubMed ID: 23496240.
    Abstract:
    A triple cascade was developed using a simple copper catalyst to trans-selectively access bicyclic isoxazolidines in a one-pot synthesis. This strategy features the in situ generation of nitrones and subsequent trapping by [3 + 2] cycloaddition. In this method, copper serves three catalytic functions: as a Lewis acid for the ene reaction, as an organometallic for aerobic oxidation, and as a Lewis acid for an endo-selective [3 + 2] cycloaddition. The successful merging of aerobic oxidation and Lewis acid catalysis demonstrated efficient cascade synergy.
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