Highly <i>trans-</i>Stereoselective Synthesis
of Bicyclic Isoxazolidines via Copper-Catalyzed Triple Cascade Catalysis
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Abstract
A triple
cascade was developed using a simple copper catalyst to <i>trans</i>-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 <i>endo</i>-selective [3 + 2] cycloaddition.
The successful merging of aerobic oxidation and Lewis acid catalysis
demonstrated efficient cascade synergy